NPASS Compound

Structure

CID205 OpenBabel06191715322D 45 51 0 0 1 0 0 0 0 0999 V2000 -1.1151 3.5108 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2847 1.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7725 -0.3773 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7416 -1.1638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0284 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2031 -1.1561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7973 2.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7973 1.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0540 2.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0540 0.7684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3107 2.0558 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3231 0.2685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7557 -0.1606 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0043 2.4168 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1505 0.7835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2853 3.2913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3107 1.1975 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1420 0.5084 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4427 1.1140 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.4504 -0.0097 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6250 1.0826 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2396 2.3711 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9789 2.0181 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7973 1.3943 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0955 1.7538 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1259 1.1081 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0808 0.7684 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8298 0.2829 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.5674 0.7684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8944 1.6408 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.9135 0.4680 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6655 1.8541 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7581 1.9081 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3196 3.9001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2347 1.3874 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9796 1.1974 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5674 -0.0899 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7386 -0.4372 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.1264 0.0235 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3011 -0.7127 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1102 1.8942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4318 -0.3288 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8241 1.1975 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0605 2.4630 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 16 1 0 0 0 0 2 34 1 0 0 0 0 3 40 1 0 0 0 0 4 41 1 0 0 0 0 5 42 1 0 0 0 0 6 43 1 0 0 0 0 7 8 2 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 2 0 0 0 0 10 17 2 0 0 0 0 11 17 1 0 0 0 0 12 19 1 0 0 0 0 12 20 1 0 0 0 0 13 18 1 0 0 0 0 13 31 1 0 0 0 0 14 30 1 0 0 0 0 14 34 1 0 0 0 0 15 40 1 0 0 0 0 16 35 2 0 0 0 0 16 45 1 0 0 0 0 17 29 1 0 0 0 0 18 21 1 0 0 0 0 18 32 1 1 0 0 0 19 30 1 1 0 0 0 19 36 1 0 0 0 0 20 32 1 1 0 0 0 20 41 1 0 0 0 0 21 27 1 0 0 0 0 21 33 1 1 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 22 33 1 1 0 0 0 23 24 1 0 0 0 0 23 42 1 6 0 0 0 24 30 1 1 0 0 0 24 32 1 0 0 0 0 25 32 1 0 0 0 0 25 34 1 0 0 0 0 26 28 1 0 0 0 0 26 33 1 6 0 0 0 26 37 1 0 0 0 0 27 31 1 1 0 0 0 27 44 1 0 0 0 0 28 31 1 1 0 0 0 28 43 1 0 0 0 0 29 38 2 0 0 0 0 29 44 1 0 0 0 0 30 15 1 6 0 0 0 31 39 1 1 0 0 0 33 45 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	631.3
Volume:	613.936
LogP:	1.188
LogD:	1.303
LogS:	-3.7
# Rotatable Bonds:	10
TPSA:	153.45
# H-Bond Aceptor:	12
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.337
Synthetic Accessibility Score:	7.266
Fsp3:	0.758
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.489
MDCK Permeability:	9.05548149603419e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.992
Human Intestinal Absorption (HIA):	0.902
20% Bioavailability (F20%):	0.311
30% Bioavailability (F30%):	0.769

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.079
Plasma Protein Binding (PPB):	18.760873794555664%
Volume Distribution (VD):	0.798
Pgp-substrate:	61.48162078857422%

ADMET: Metabolism

CYP1A2-inhibitor:	0.006
CYP1A2-substrate:	0.492
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.608
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.01
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.165
CYP3A4-inhibitor:	0.243
CYP3A4-substrate:	0.444

ADMET: Excretion

Clearance (CL):	2.779
Half-life (T1/2):	0.586

ADMET: Toxicity

hERG Blockers:	0.793
Human Hepatotoxicity (H-HT):	0.983
Drug-inuced Liver Injury (DILI):	0.445
AMES Toxicity:	0.055
Rat Oral Acute Toxicity:	0.505
Maximum Recommended Daily Dose:	0.48
Skin Sensitization:	0.172
Carcinogencity:	0.008
Eye Corrosion:	0.003
Eye Irritation:	0.006
Respiratory Toxicity:	0.963

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC205

Natural Product ID:	NPC205
*Common Name:**	XUHJBXVYNBQQBD-TUWOXVOMSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XUHJBXVYNBQQBD-TUWOXVOMSA-N
Standard InCHI:	InChI=1S/C33H45NO11/c1-16(35)45-33-21-18(13-31(39,28(43-6)26(33)37)27(21)44-29(38)17-10-8-7-9-11-17)32-20(41-4)12-19(36)30(15-40-3)14-34(2)25(32)22(33)23(42-5)24(30)32/h7-11,18-28,36-37,39H,12-15H2,1-6H3/t18-,19-,20+,21-,22+,23+,24-,25?,26+,27-,28+,30+,31-,32+,33-/m1/s1
SMILES:	CC(=O)O[C@]12[C@@H]3[C@@H](C[C@@]([C@@H]3OC(=O)c3ccccc3)([C@H]([C@@H]2O)OC)O)[C@]23[C@H](C[C@H]([C@]4(CN(C)C3[C@@H]1[C@@H]([C@@H]24)OC)COC)O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3400310
PubChem CID:	441747
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003788] Aconitane-type diterpenoid alkaloids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	tuber	n.a.	PMID[12913245]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1293938]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16181762]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	roots	n.a.	n.a.	PMID[18044843]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22223386]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Lateral roots	n.a.	n.a.	PMID[22607495]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22628040]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[22907155]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23225552]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23707213]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[23707213]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24170571]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24170571]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24190290]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[24190290]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24793215]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	PMID[27761113]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	Europe PMC[300080]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Europe PMC[300080]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30892884]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4902	Aconitum carmichaelii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4893	Aconitum ciliare	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14688	Aconitum triphyllum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8847	Aconitum kusnezoffii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7490	Aconitum japonicum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
GI50	4
Others	1

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	GI50	>	20000.0	nM	PMID[455053]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	>	20000.0	nM	PMID[455053]
NPT91	Cell Line	KB	Homo sapiens	GI50	>	20000.0	nM	PMID[455053]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	>	20000.0	nM	PMID[455053]
NPT2	Others	Unspecified		RatioGI50	>	20.0	n.a.	PMID[455053]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC205 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	282
0.1-0.2	1154
0.2-0.3	2666
0.3-0.4	6790
0.4-0.5	15663
0.5-0.6	13702
0.6-0.7	1983
0.7-0.8	407
0.8-0.85	10
0.85-0.9	6
0.9-0.95	7
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC281470
1.0	High Similarity	NPC166521
1.0	High Similarity	NPC184195
1.0	High Similarity	NPC124690
1.0	High Similarity	NPC172769
0.9826	High Similarity	NPC163578
0.9826	High Similarity	NPC108276
0.9767	High Similarity	NPC40539
0.9243	High Similarity	NPC476496
0.9086	High Similarity	NPC476495
0.9086	High Similarity	NPC106840
0.9086	High Similarity	NPC94687
0.9032	High Similarity	NPC326895
0.8622	High Similarity	NPC223590
0.8579	High Similarity	NPC140311
0.852	High Similarity	NPC473837
0.8492	Intermediate Similarity	NPC106593
0.845	Intermediate Similarity	NPC473667
0.8252	Intermediate Similarity	NPC473486
0.8252	Intermediate Similarity	NPC475316
0.8204	Intermediate Similarity	NPC470631
0.8204	Intermediate Similarity	NPC35390
0.8204	Intermediate Similarity	NPC473781
0.8103	Intermediate Similarity	NPC476500
0.7809	Intermediate Similarity	NPC322048
0.7809	Intermediate Similarity	NPC318447
0.7803	Intermediate Similarity	NPC478263
0.7802	Intermediate Similarity	NPC30171
0.7753	Intermediate Similarity	NPC326235
0.7753	Intermediate Similarity	NPC323001
0.7746	Intermediate Similarity	NPC184817
0.7746	Intermediate Similarity	NPC177940
0.7746	Intermediate Similarity	NPC472568
0.7746	Intermediate Similarity	NPC96903
0.7746	Intermediate Similarity	NPC478264
0.7746	Intermediate Similarity	NPC472572
0.7746	Intermediate Similarity	NPC476973
0.7746	Intermediate Similarity	NPC158663
0.7746	Intermediate Similarity	NPC472575
0.7746	Intermediate Similarity	NPC470159
0.7746	Intermediate Similarity	NPC70403
0.7746	Intermediate Similarity	NPC473088
0.7746	Intermediate Similarity	NPC469349
0.7746	Intermediate Similarity	NPC200471
0.7746	Intermediate Similarity	NPC171525
0.7746	Intermediate Similarity	NPC174982
0.7746	Intermediate Similarity	NPC470157
0.7746	Intermediate Similarity	NPC472571
0.7746	Intermediate Similarity	NPC471104
0.7746	Intermediate Similarity	NPC29704
0.774	Intermediate Similarity	NPC471135
0.7735	Intermediate Similarity	NPC253738
0.7735	Intermediate Similarity	NPC478124
0.7722	Intermediate Similarity	NPC471138
0.7722	Intermediate Similarity	NPC476750
0.7722	Intermediate Similarity	NPC326328
0.7722	Intermediate Similarity	NPC323356
0.7722	Intermediate Similarity	NPC309991
0.7714	Intermediate Similarity	NPC92293
0.7714	Intermediate Similarity	NPC301556
0.7714	Intermediate Similarity	NPC266265
0.7714	Intermediate Similarity	NPC471101
0.7714	Intermediate Similarity	NPC270590
0.7705	Intermediate Similarity	NPC475567
0.7705	Intermediate Similarity	NPC473468
0.7705	Intermediate Similarity	NPC477491
0.7705	Intermediate Similarity	NPC476749
0.7705	Intermediate Similarity	NPC473557
0.7701	Intermediate Similarity	NPC473602
0.7701	Intermediate Similarity	NPC312393
0.7688	Intermediate Similarity	NPC95810
0.7688	Intermediate Similarity	NPC475759
0.7688	Intermediate Similarity	NPC470152
0.7688	Intermediate Similarity	NPC188865
0.7688	Intermediate Similarity	NPC472570
0.7688	Intermediate Similarity	NPC95265
0.7688	Intermediate Similarity	NPC241951
0.7688	Intermediate Similarity	NPC472569
0.7688	Intermediate Similarity	NPC25768
0.7688	Intermediate Similarity	NPC11685
0.7688	Intermediate Similarity	NPC70716
0.7688	Intermediate Similarity	NPC163719
0.7688	Intermediate Similarity	NPC57628
0.7688	Intermediate Similarity	NPC125106
0.7688	Intermediate Similarity	NPC472573
0.7688	Intermediate Similarity	NPC475122
0.7688	Intermediate Similarity	NPC476974
0.767	Intermediate Similarity	NPC476173
0.7667	Intermediate Similarity	NPC319404
0.7667	Intermediate Similarity	NPC476784
0.7663	Intermediate Similarity	NPC475175
0.7663	Intermediate Similarity	NPC475198
0.7663	Intermediate Similarity	NPC475531
0.7657	Intermediate Similarity	NPC281717
0.7657	Intermediate Similarity	NPC327031
0.7654	Intermediate Similarity	NPC290683
0.7654	Intermediate Similarity	NPC475638
0.7654	Intermediate Similarity	NPC475548
0.7644	Intermediate Similarity	NPC472556
0.763	Intermediate Similarity	NPC163087
0.7616	Intermediate Similarity	NPC16912
0.7616	Intermediate Similarity	NPC118080
0.7616	Intermediate Similarity	NPC41481
0.7616	Intermediate Similarity	NPC472576
0.7616	Intermediate Similarity	NPC291599
0.7616	Intermediate Similarity	NPC27377
0.7616	Intermediate Similarity	NPC97947
0.7616	Intermediate Similarity	NPC87448
0.7614	Intermediate Similarity	NPC76103
0.7614	Intermediate Similarity	NPC476975
0.7596	Intermediate Similarity	NPC478125
0.7584	Intermediate Similarity	NPC477905
0.7581	Intermediate Similarity	NPC477488
0.7571	Intermediate Similarity	NPC470245
0.7571	Intermediate Similarity	NPC473214
0.7558	Intermediate Similarity	NPC97667
0.7558	Intermediate Similarity	NPC171207
0.7558	Intermediate Similarity	NPC100913
0.7558	Intermediate Similarity	NPC90614
0.7558	Intermediate Similarity	NPC275592
0.7556	Intermediate Similarity	NPC70344
0.7542	Intermediate Similarity	NPC472658
0.7542	Intermediate Similarity	NPC472657
0.7528	Intermediate Similarity	NPC96308
0.7528	Intermediate Similarity	NPC470153
0.7514	Intermediate Similarity	NPC473215
0.7513	Intermediate Similarity	NPC327699
0.75	Intermediate Similarity	NPC240115
0.75	Intermediate Similarity	NPC132599
0.75	Intermediate Similarity	NPC469730
0.75	Intermediate Similarity	NPC474935
0.75	Intermediate Similarity	NPC473632
0.75	Intermediate Similarity	NPC473611
0.7486	Intermediate Similarity	NPC34943
0.7486	Intermediate Similarity	NPC476077
0.7486	Intermediate Similarity	NPC472548
0.7472	Intermediate Similarity	NPC31829
0.7471	Intermediate Similarity	NPC34012
0.746	Intermediate Similarity	NPC203005
0.7458	Intermediate Similarity	NPC473760
0.7457	Intermediate Similarity	NPC473085
0.7457	Intermediate Similarity	NPC473758
0.7457	Intermediate Similarity	NPC473081
0.7457	Intermediate Similarity	NPC476094
0.7457	Intermediate Similarity	NPC473060
0.7457	Intermediate Similarity	NPC200592
0.7457	Intermediate Similarity	NPC4341
0.7457	Intermediate Similarity	NPC147880
0.7457	Intermediate Similarity	NPC473613
0.7457	Intermediate Similarity	NPC473109
0.7457	Intermediate Similarity	NPC43241
0.7457	Intermediate Similarity	NPC48017
0.7457	Intermediate Similarity	NPC211137
0.7457	Intermediate Similarity	NPC473112
0.7457	Intermediate Similarity	NPC472547
0.7457	Intermediate Similarity	NPC184747
0.7446	Intermediate Similarity	NPC472574
0.743	Intermediate Similarity	NPC62792
0.743	Intermediate Similarity	NPC478123
0.7429	Intermediate Similarity	NPC473673
0.7429	Intermediate Similarity	NPC139067
0.7429	Intermediate Similarity	NPC246480
0.7429	Intermediate Similarity	NPC91703
0.7429	Intermediate Similarity	NPC475429
0.7429	Intermediate Similarity	NPC177340
0.7429	Intermediate Similarity	NPC270498
0.7429	Intermediate Similarity	NPC191082
0.7429	Intermediate Similarity	NPC147217
0.7424	Intermediate Similarity	NPC36607
0.7414	Intermediate Similarity	NPC224491
0.7403	Intermediate Similarity	NPC228204
0.7403	Intermediate Similarity	NPC26033
0.7403	Intermediate Similarity	NPC472549
0.7403	Intermediate Similarity	NPC34066
0.7401	Intermediate Similarity	NPC209592
0.7401	Intermediate Similarity	NPC48599
0.7401	Intermediate Similarity	NPC20255
0.7399	Intermediate Similarity	NPC214550
0.7399	Intermediate Similarity	NPC210591
0.7399	Intermediate Similarity	NPC475652
0.7386	Intermediate Similarity	NPC51314
0.7386	Intermediate Similarity	NPC67777
0.7374	Intermediate Similarity	NPC7095
0.7371	Intermediate Similarity	NPC192658
0.7371	Intermediate Similarity	NPC475135
0.7368	Intermediate Similarity	NPC48929
0.7363	Intermediate Similarity	NPC106895
0.7348	Intermediate Similarity	NPC472005
0.7348	Intermediate Similarity	NPC256142
0.7348	Intermediate Similarity	NPC472030
0.7348	Intermediate Similarity	NPC304876
0.7348	Intermediate Similarity	NPC158333
0.7348	Intermediate Similarity	NPC242262
0.7348	Intermediate Similarity	NPC472022
0.7348	Intermediate Similarity	NPC473414
0.7348	Intermediate Similarity	NPC237549
0.7348	Intermediate Similarity	NPC257213
0.7348	Intermediate Similarity	NPC1173
0.7348	Intermediate Similarity	NPC249471
0.7348	Intermediate Similarity	NPC265395

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC205 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	187
0.1-0.2	592
0.2-0.3	1221
0.3-0.4	2658
0.4-0.5	3188
0.5-0.6	1090
0.6-0.7	210
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8973	High Similarity	NPD7497	Discontinued
0.7594	Intermediate Similarity	NPD8470	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8361	Approved
0.7296	Intermediate Similarity	NPD8435	Approved
0.7296	Intermediate Similarity	NPD8360	Approved
0.7268	Intermediate Similarity	NPD8407	Phase 2
0.725	Intermediate Similarity	NPD8485	Approved
0.7202	Intermediate Similarity	NPD8368	Discontinued
0.7194	Intermediate Similarity	NPD8424	Clinical (unspecified phase)
0.7173	Intermediate Similarity	NPD7799	Discontinued
0.7159	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8486	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD7488	Clinical (unspecified phase)
0.7056	Intermediate Similarity	NPD7236	Approved
0.7049	Intermediate Similarity	NPD7239	Suspended
0.7	Intermediate Similarity	NPD7274	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8319	Approved
0.6923	Remote Similarity	NPD8320	Phase 1
0.6919	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.69	Remote Similarity	NPD7906	Approved
0.6885	Remote Similarity	NPD8389	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6997	Phase 2
0.6857	Remote Similarity	NPD7715	Approved
0.6857	Remote Similarity	NPD7714	Approved
0.6837	Remote Similarity	NPD7047	Phase 3
0.6829	Remote Similarity	NPD2974	Approved
0.6829	Remote Similarity	NPD2975	Approved
0.6829	Remote Similarity	NPD2973	Approved
0.6825	Remote Similarity	NPD7701	Phase 2
0.6812	Remote Similarity	NPD4580	Approved
0.6798	Remote Similarity	NPD2569	Approved
0.6798	Remote Similarity	NPD2567	Approved
0.6788	Remote Similarity	NPD3051	Approved
0.6779	Remote Similarity	NPD2493	Approved
0.6779	Remote Similarity	NPD2494	Approved
0.6766	Remote Similarity	NPD4663	Approved
0.6762	Remote Similarity	NPD4583	Approved
0.6762	Remote Similarity	NPD4582	Approved
0.6761	Remote Similarity	NPD7713	Phase 3
0.6758	Remote Similarity	NPD7907	Approved
0.6746	Remote Similarity	NPD3057	Approved
0.6734	Remote Similarity	NPD8658	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4107	Approved
0.6718	Remote Similarity	NPD4481	Phase 3
0.6714	Remote Similarity	NPD4002	Approved
0.6714	Remote Similarity	NPD4004	Approved
0.67	Remote Similarity	NPD7310	Approved
0.67	Remote Similarity	NPD7311	Approved
0.67	Remote Similarity	NPD7313	Approved
0.67	Remote Similarity	NPD7312	Approved
0.6699	Remote Similarity	NPD3450	Approved
0.6699	Remote Similarity	NPD3452	Approved
0.6698	Remote Similarity	NPD8462	Phase 1
0.6697	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3533	Approved
0.6667	Remote Similarity	NPD4111	Phase 1
0.6667	Remote Similarity	NPD2575	Approved
0.6667	Remote Similarity	NPD7309	Approved
0.6667	Remote Similarity	NPD4665	Approved
0.6667	Remote Similarity	NPD2970	Approved
0.6667	Remote Similarity	NPD2969	Approved
0.6667	Remote Similarity	NPD2972	Approved
0.6667	Remote Similarity	NPD2490	Approved
0.6667	Remote Similarity	NPD2488	Approved
0.6649	Remote Similarity	NPD8127	Discontinued
0.6635	Remote Similarity	NPD7699	Phase 2
0.6635	Remote Similarity	NPD7700	Phase 2
0.6619	Remote Similarity	NPD4482	Phase 3
0.6617	Remote Similarity	NPD2968	Approved
0.6617	Remote Similarity	NPD2971	Approved
0.6617	Remote Similarity	NPD4577	Approved
0.6617	Remote Similarity	NPD4578	Approved
0.6615	Remote Similarity	NPD7057	Phase 3
0.6615	Remote Similarity	NPD7058	Phase 2
0.6602	Remote Similarity	NPD6213	Phase 3
0.6602	Remote Similarity	NPD6212	Phase 3
0.6602	Remote Similarity	NPD6214	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD2491	Approved
0.6575	Remote Similarity	NPD8404	Phase 2
0.6574	Remote Similarity	NPD5676	Approved
0.6573	Remote Similarity	NPD7999	Approved
0.657	Remote Similarity	NPD6535	Approved
0.657	Remote Similarity	NPD6534	Approved
0.6548	Remote Similarity	NPD2489	Approved
0.6548	Remote Similarity	NPD27	Approved
0.6548	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6536	Remote Similarity	NPD6309	Approved
0.6536	Remote Similarity	NPD6311	Approved
0.6536	Remote Similarity	NPD6310	Approved
0.6535	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD7874	Approved
0.6528	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD8285	Discontinued
0.652	Remote Similarity	NPD8150	Discontinued
0.6517	Remote Similarity	NPD5039	Approved
0.6509	Remote Similarity	NPD3448	Approved
0.6497	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6497	Remote Similarity	NPD2613	Approved
0.6495	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD7930	Approved
0.6471	Remote Similarity	NPD5036	Approved
0.6471	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.6459	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5667	Approved
0.6447	Remote Similarity	NPD7315	Approved
0.6444	Remote Similarity	NPD5119	Approved
0.6444	Remote Similarity	NPD5121	Approved
0.6444	Remote Similarity	NPD5120	Approved
0.6439	Remote Similarity	NPD5037	Approved
0.6439	Remote Similarity	NPD5038	Approved
0.6432	Remote Similarity	NPD5006	Approved
0.6432	Remote Similarity	NPD6823	Phase 2
0.6432	Remote Similarity	NPD5005	Approved
0.6425	Remote Similarity	NPD3808	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7801	Approved
0.642	Remote Similarity	NPD2160	Approved
0.642	Remote Similarity	NPD2626	Approved
0.642	Remote Similarity	NPD2628	Approved
0.642	Remote Similarity	NPD2625	Approved
0.642	Remote Similarity	NPD2159	Approved
0.642	Remote Similarity	NPD2627	Approved
0.6418	Remote Similarity	NPD4956	Approved
0.6415	Remote Similarity	NPD6778	Approved
0.6415	Remote Similarity	NPD6779	Approved
0.6415	Remote Similarity	NPD6780	Approved
0.6415	Remote Similarity	NPD6782	Approved
0.6415	Remote Similarity	NPD6781	Approved
0.6415	Remote Similarity	NPD6776	Approved
0.6415	Remote Similarity	NPD6777	Approved
0.6406	Remote Similarity	NPD6385	Approved
0.6406	Remote Similarity	NPD6677	Suspended
0.6406	Remote Similarity	NPD6386	Approved
0.6404	Remote Similarity	NPD5203	Approved
0.6404	Remote Similarity	NPD7549	Discontinued
0.6404	Remote Similarity	NPD4617	Approved
0.6404	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4620	Approved
0.6404	Remote Similarity	NPD7962	Phase 2
0.6404	Remote Similarity	NPD5201	Approved
0.6402	Remote Similarity	NPD7696	Phase 3
0.6402	Remote Similarity	NPD7698	Approved
0.6402	Remote Similarity	NPD6273	Approved
0.6402	Remote Similarity	NPD7697	Approved
0.64	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.64	Remote Similarity	NPD5159	Phase 2
0.64	Remote Similarity	NPD5157	Phase 1
0.6398	Remote Similarity	NPD4420	Approved
0.6389	Remote Similarity	NPD3087	Approved
0.6389	Remote Similarity	NPD4745	Approved
0.6389	Remote Similarity	NPD2573	Approved
0.6389	Remote Similarity	NPD3616	Approved
0.6389	Remote Similarity	NPD2572	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD3614	Approved
0.6389	Remote Similarity	NPD3088	Approved
0.6389	Remote Similarity	NPD2566	Approved
0.6389	Remote Similarity	NPD4746	Phase 3
0.6389	Remote Similarity	NPD3090	Approved
0.6389	Remote Similarity	NPD2574	Discontinued
0.6389	Remote Similarity	NPD3089	Approved
0.6389	Remote Similarity	NPD3615	Approved
0.6389	Remote Similarity	NPD2570	Approved
0.6389	Remote Similarity	NPD2571	Approved
0.6388	Remote Similarity	NPD8059	Phase 3
0.6388	Remote Similarity	NPD8058	Clinical (unspecified phase)
0.6384	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6374	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6372	Remote Similarity	NPD7871	Phase 2
0.6372	Remote Similarity	NPD4040	Phase 1
0.6372	Remote Similarity	NPD7870	Phase 2
0.6364	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6359	Remote Similarity	NPD8434	Phase 2
0.6355	Remote Similarity	NPD7038	Approved
0.6355	Remote Similarity	NPD7039	Approved
0.6355	Remote Similarity	NPD7685	Pre-registration
0.6347	Remote Similarity	NPD7783	Phase 2
0.6347	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6343	Remote Similarity	NPD8161	Suspended
0.6341	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6333	Remote Similarity	NPD4619	Approved
0.6333	Remote Similarity	NPD4621	Approved
0.6327	Remote Similarity	NPD8005	Clinical (unspecified phase)
0.6326	Remote Similarity	NPD7435	Discontinued
0.6319	Remote Similarity	NPD4685	Phase 3
0.6319	Remote Similarity	NPD4684	Phase 3
0.6319	Remote Similarity	NPD4686	Approved
0.6318	Remote Similarity	NPD7177	Discontinued
0.6316	Remote Similarity	NPD7296	Approved
0.6309	Remote Similarity	NPD7048	Phase 3
0.63	Remote Similarity	NPD2898	Approved
0.6298	Remote Similarity	NPD7961	Discontinued
0.6291	Remote Similarity	NPD7565	Approved
0.6289	Remote Similarity	NPD6844	Discontinued
0.6286	Remote Similarity	NPD2612	Approved
0.6286	Remote Similarity	NPD4217	Approved
0.6286	Remote Similarity	NPD3132	Approved
0.6286	Remote Similarity	NPD4218	Approved
0.6286	Remote Similarity	NPD2609	Approved
0.6286	Remote Similarity	NPD2611	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data