NPASS Compound

Structure

NPC473838 OpenBabel07101718312D 48 54 0 0 1 0 0 0 0 0999 V2000 0.9747 -1.8201 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0001 -0.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3210 -2.5402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6299 -2.9604 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3532 -2.2864 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0920 1.4552 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2117 1.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5602 1.1568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7320 1.9849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7434 0.5929 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1681 2.1681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7434 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5752 2.1681 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5602 -0.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0114 1.9849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2117 -1.0435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5317 1.6364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7320 -1.3920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1832 1.1568 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4397 -2.9051 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0988 -0.8511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1681 -1.5752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7497 -2.5365 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3888 -0.5870 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7403 0.7243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5752 -1.5752 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.7693 -0.3465 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6071 -1.4441 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8894 -2.9995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4744 -0.3986 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5331 -0.9556 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1702 -0.4447 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.7693 -2.5417 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5331 -1.9326 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.5929 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1832 -2.3243 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3217 -0.2590 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1832 -0.5639 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2352 -3.4722 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6974 0.9203 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7582 -3.9676 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9867 -3.4942 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7914 -2.2567 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4315 -0.2026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3792 -1.4441 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2144 0.0249 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4068 0.2598 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 21 2 0 0 0 0 2 21 1 0 0 0 0 5 24 1 0 0 0 0 6 25 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 12 1 0 0 0 0 11 13 1 0 0 0 0 12 14 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 15 17 1 0 0 0 0 16 18 1 0 0 0 0 17 19 2 0 0 0 0 18 22 1 0 0 0 0 19 35 1 0 0 0 0 20 34 1 0 0 0 0 20 39 1 0 0 0 0 21 37 1 0 0 0 0 22 3 1 6 0 0 0 22 26 1 0 0 0 0 23 4 1 6 0 0 0 23 26 1 0 0 0 0 23 29 1 0 0 0 0 24 30 1 0 0 0 0 24 38 1 1 0 0 0 25 40 2 0 0 0 0 25 44 1 0 0 0 0 26 28 1 0 0 0 0 27 31 1 0 0 0 0 27 32 1 0 0 0 0 27 38 1 0 0 0 0 28 36 1 0 0 0 0 28 38 1 0 0 0 0 29 36 1 0 0 0 0 29 41 2 0 0 0 0 30 37 1 0 0 0 0 30 44 1 0 0 0 0 31 34 1 0 0 0 0 31 45 1 0 0 0 0 32 37 1 0 0 0 0 32 46 1 0 0 0 0 33 34 1 0 0 0 0 33 36 1 0 0 0 0 33 42 1 0 0 0 0 34 45 1 0 0 0 0 35 46 1 0 0 0 0 35 47 1 0 0 0 0 35 48 1 0 0 0 0 36 43 1 0 0 0 0 37 47 1 0 0 0 0 38 48 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	672.39
Volume:	683.265
LogP:	5.617
LogD:	4.164
LogS:	-3.726
# Rotatable Bonds:	4
TPSA:	144.28
# H-Bond Aceptor:	10
# H-Bond Donor:	3
# Rings:	7
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.222
Synthetic Accessibility Score:	4.738
Fsp3:	0.842
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:	-5.048
MDCK Permeability:	3.676975393318571e-05
Pgp-inhibitor:	0.972
Pgp-substrate:	0.932
Human Intestinal Absorption (HIA):	0.336
20% Bioavailability (F20%):	0.941
30% Bioavailability (F30%):	0.26

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.211
Plasma Protein Binding (PPB):	98.2402114868164%
Volume Distribution (VD):	1.498
Pgp-substrate:	3.126215934753418%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.928
CYP2C19-inhibitor:	0.033
CYP2C19-substrate:	0.655
CYP2C9-inhibitor:	0.652
CYP2C9-substrate:	0.003
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.042
CYP3A4-inhibitor:	0.892
CYP3A4-substrate:	0.449

ADMET: Excretion

Clearance (CL):	6.325
Half-life (T1/2):	0.37

ADMET: Toxicity

hERG Blockers:	0.673
Human Hepatotoxicity (H-HT):	0.972
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.096
Rat Oral Acute Toxicity:	0.841
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.395
Carcinogencity:	0.448
Eye Corrosion:	0.009
Eye Irritation:	0.012
Respiratory Toxicity:	0.99

Download Data

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

Natural Product: NPC473838

Natural Product ID:	NPC473838
*Common Name:**	VDECHLXUERWMCP-LFWQBVMASA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VDECHLXUERWMCP-LFWQBVMASA-N
Standard InCHI:	InChI=1S/C38H56O10/c1-21(2)37-30(44-25(6)40)24(5)38-27-31-34(20-39,45-31)33(42)36(43)28(38)26(23(4)29(36)41)22(3)18-16-14-12-10-8-7-9-11-13-15-17-19-35(47-37,48-38)46-32(27)37/h17,19,22-24,26-28,30-33,39,42-43H,1,7-16,18,20H2,2-6H3/b19-17+/t22-,23-,24+,26-,27-,28+,30+,31-,32+,33+,34-,35+,36+,37+,38+/m0/s1
SMILES:	CC1CCCCCCCCCCCC=CC23OC4C5C6C(O6)(C(C7(C(C1C(C7=O)C)C5(O2)C(C(C4(O3)C(=C)C)OC(=O)C)C)O)O)CO
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL453165
PubChem CID:	44559857
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003494] Rhamnofolane and daphnane diterpenoids

*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
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11000015]
NPO33116	synaptolepis retusa	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]
NPO32646	synaptolepis kirkii	Species	Thymelaeaceae	Eukaryota	roots	n.a.	n.a.	PMID[3210015]

☑ 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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.01	nmol	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	100.0	/nmol	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	33.0	%	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.0	%	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	100.0	%	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	27.0	%	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.33	n.a.	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.0	n.a.	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	4.4	n.a.	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	0.6	n.a.	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	99.0	%	PMID[565709]
NPT32	Organism	Mus musculus	Mus musculus	Survival	=	94.0	%	PMID[565709]

☑ 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 NPC473838 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	301
0.1-0.2	1704
0.2-0.3	4872
0.3-0.4	8507
0.4-0.5	13258
0.5-0.6	7460
0.6-0.7	5189
0.7-0.8	1317
0.8-0.85	45
0.85-0.9	19
0.9-0.95	21
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC475389
0.9832	High Similarity	NPC476091
0.9832	High Similarity	NPC476078
0.9431	High Similarity	NPC180902
0.9431	High Similarity	NPC475139
0.928	High Similarity	NPC100017
0.928	High Similarity	NPC475500
0.928	High Similarity	NPC471137
0.928	High Similarity	NPC473548
0.928	High Similarity	NPC475154
0.928	High Similarity	NPC223356
0.928	High Similarity	NPC182266
0.928	High Similarity	NPC471136
0.9268	High Similarity	NPC162495
0.9244	High Similarity	NPC142882
0.9134	High Similarity	NPC68282
0.912	High Similarity	NPC474508
0.912	High Similarity	NPC473485
0.9106	High Similarity	NPC168849
0.9106	High Similarity	NPC475273
0.904	High Similarity	NPC475606
0.904	High Similarity	NPC475314
0.904	High Similarity	NPC477189
0.904	High Similarity	NPC251564
0.9024	High Similarity	NPC217901
0.8862	High Similarity	NPC473802
0.879	High Similarity	NPC473919
0.879	High Similarity	NPC473709
0.872	High Similarity	NPC471939
0.8651	High Similarity	NPC471940
0.8618	High Similarity	NPC317635
0.8618	High Similarity	NPC329008
0.8468	Intermediate Similarity	NPC472004
0.8397	Intermediate Similarity	NPC471234
0.8385	Intermediate Similarity	NPC471855
0.832	Intermediate Similarity	NPC143755
0.8295	Intermediate Similarity	NPC236999
0.8295	Intermediate Similarity	NPC270109
0.8248	Intermediate Similarity	NPC471172
0.824	Intermediate Similarity	NPC19028
0.824	Intermediate Similarity	NPC9674
0.824	Intermediate Similarity	NPC470186
0.824	Intermediate Similarity	NPC472667
0.8231	Intermediate Similarity	NPC475371
0.8231	Intermediate Similarity	NPC471407
0.8231	Intermediate Similarity	NPC470851
0.8231	Intermediate Similarity	NPC231529
0.8217	Intermediate Similarity	NPC42399
0.8217	Intermediate Similarity	NPC470780
0.8217	Intermediate Similarity	NPC287423
0.8197	Intermediate Similarity	NPC471933
0.8189	Intermediate Similarity	NPC257017
0.8189	Intermediate Similarity	NPC222688
0.8189	Intermediate Similarity	NPC162009
0.8188	Intermediate Similarity	NPC48813
0.8188	Intermediate Similarity	NPC194854
0.8182	Intermediate Similarity	NPC88668
0.8168	Intermediate Similarity	NPC471170
0.8154	Intermediate Similarity	NPC311534
0.8154	Intermediate Similarity	NPC473620
0.8154	Intermediate Similarity	NPC470850
0.8148	Intermediate Similarity	NPC290746
0.8148	Intermediate Similarity	NPC79250
0.814	Intermediate Similarity	NPC222307
0.814	Intermediate Similarity	NPC473635
0.8129	Intermediate Similarity	NPC16729
0.8129	Intermediate Similarity	NPC475462
0.8125	Intermediate Similarity	NPC471392
0.8125	Intermediate Similarity	NPC472399
0.8125	Intermediate Similarity	NPC43252
0.8125	Intermediate Similarity	NPC135038
0.811	Intermediate Similarity	NPC477046
0.811	Intermediate Similarity	NPC102822
0.811	Intermediate Similarity	NPC310511
0.8106	Intermediate Similarity	NPC472769
0.8102	Intermediate Similarity	NPC5153
0.8102	Intermediate Similarity	NPC48414
0.8092	Intermediate Similarity	NPC470880
0.8092	Intermediate Similarity	NPC104382
0.8092	Intermediate Similarity	NPC175186
0.8082	Intermediate Similarity	NPC154675
0.8077	Intermediate Similarity	NPC146456
0.8077	Intermediate Similarity	NPC469757
0.8077	Intermediate Similarity	NPC298841
0.8077	Intermediate Similarity	NPC470882
0.8077	Intermediate Similarity	NPC117702
0.8077	Intermediate Similarity	NPC471357
0.8077	Intermediate Similarity	NPC473253
0.8065	Intermediate Similarity	NPC178289
0.8047	Intermediate Similarity	NPC19464
0.8047	Intermediate Similarity	NPC65858
0.8045	Intermediate Similarity	NPC475487
0.8031	Intermediate Similarity	NPC471406
0.8031	Intermediate Similarity	NPC4548
0.803	Intermediate Similarity	NPC173347
0.8	Intermediate Similarity	NPC174367
0.8	Intermediate Similarity	NPC181999
0.8	Intermediate Similarity	NPC59288
0.8	Intermediate Similarity	NPC106228
0.8	Intermediate Similarity	NPC138372
0.8	Intermediate Similarity	NPC293112
0.8	Intermediate Similarity	NPC47113
0.7984	Intermediate Similarity	NPC469352
0.7984	Intermediate Similarity	NPC11895
0.7984	Intermediate Similarity	NPC41129
0.7984	Intermediate Similarity	NPC267822
0.797	Intermediate Similarity	NPC231240
0.797	Intermediate Similarity	NPC470185
0.797	Intermediate Similarity	NPC473805
0.797	Intermediate Similarity	NPC473519
0.7969	Intermediate Similarity	NPC472000
0.7969	Intermediate Similarity	NPC471999
0.7969	Intermediate Similarity	NPC52839
0.7969	Intermediate Similarity	NPC472401
0.7955	Intermediate Similarity	NPC251866
0.7955	Intermediate Similarity	NPC473593
0.7955	Intermediate Similarity	NPC471358
0.7955	Intermediate Similarity	NPC180079
0.7955	Intermediate Similarity	NPC469755
0.7955	Intermediate Similarity	NPC284406
0.7955	Intermediate Similarity	NPC219085
0.7955	Intermediate Similarity	NPC471361
0.7955	Intermediate Similarity	NPC469754
0.7955	Intermediate Similarity	NPC476966
0.7955	Intermediate Similarity	NPC89514
0.7955	Intermediate Similarity	NPC10823
0.7955	Intermediate Similarity	NPC469753
0.7955	Intermediate Similarity	NPC469752
0.7955	Intermediate Similarity	NPC476851
0.7955	Intermediate Similarity	NPC197707
0.7955	Intermediate Similarity	NPC6108
0.7955	Intermediate Similarity	NPC9499
0.7955	Intermediate Similarity	NPC86159
0.7955	Intermediate Similarity	NPC17896
0.7955	Intermediate Similarity	NPC471352
0.7955	Intermediate Similarity	NPC471360
0.7955	Intermediate Similarity	NPC70542
0.7955	Intermediate Similarity	NPC469751
0.7955	Intermediate Similarity	NPC472770
0.7955	Intermediate Similarity	NPC471359
0.7953	Intermediate Similarity	NPC312536
0.7953	Intermediate Similarity	NPC477071
0.7939	Intermediate Similarity	NPC473265
0.7937	Intermediate Similarity	NPC476713
0.7937	Intermediate Similarity	NPC476712
0.7937	Intermediate Similarity	NPC473590
0.7937	Intermediate Similarity	NPC176513
0.7937	Intermediate Similarity	NPC296822
0.7937	Intermediate Similarity	NPC470775
0.7926	Intermediate Similarity	NPC171619
0.7926	Intermediate Similarity	NPC256618
0.7926	Intermediate Similarity	NPC219058
0.7923	Intermediate Similarity	NPC473255
0.7923	Intermediate Similarity	NPC145238
0.7923	Intermediate Similarity	NPC241456
0.7923	Intermediate Similarity	NPC169818
0.7923	Intermediate Similarity	NPC81736
0.7923	Intermediate Similarity	NPC172154
0.7923	Intermediate Similarity	NPC32868
0.7923	Intermediate Similarity	NPC8369
0.7923	Intermediate Similarity	NPC469790
0.7923	Intermediate Similarity	NPC470922
0.792	Intermediate Similarity	NPC73314
0.7914	Intermediate Similarity	NPC471171
0.791	Intermediate Similarity	NPC146857
0.791	Intermediate Similarity	NPC247190
0.791	Intermediate Similarity	NPC102015
0.791	Intermediate Similarity	NPC32793
0.791	Intermediate Similarity	NPC469749
0.791	Intermediate Similarity	NPC116075
0.791	Intermediate Similarity	NPC316915
0.7907	Intermediate Similarity	NPC170538
0.7907	Intermediate Similarity	NPC269642
0.7903	Intermediate Similarity	NPC473877
0.7903	Intermediate Similarity	NPC280782
0.7895	Intermediate Similarity	NPC279478
0.7895	Intermediate Similarity	NPC476852
0.7895	Intermediate Similarity	NPC241935
0.7895	Intermediate Similarity	NPC213634
0.7891	Intermediate Similarity	NPC145182
0.7891	Intermediate Similarity	NPC157252
0.7891	Intermediate Similarity	NPC471128
0.7891	Intermediate Similarity	NPC112038
0.7891	Intermediate Similarity	NPC471126
0.7891	Intermediate Similarity	NPC251226
0.7891	Intermediate Similarity	NPC475003
0.7886	Intermediate Similarity	NPC475134
0.7886	Intermediate Similarity	NPC475563
0.7879	Intermediate Similarity	NPC477490
0.7879	Intermediate Similarity	NPC188291
0.7879	Intermediate Similarity	NPC114306
0.7879	Intermediate Similarity	NPC245094
0.7874	Intermediate Similarity	NPC204552
0.7874	Intermediate Similarity	NPC475372
0.7874	Intermediate Similarity	NPC124676
0.7874	Intermediate Similarity	NPC188667
0.7874	Intermediate Similarity	NPC257457
0.7874	Intermediate Similarity	NPC146280
0.7874	Intermediate Similarity	NPC311554
0.7863	Intermediate Similarity	NPC470973

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 NPC473838 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	253
0.1-0.2	1926
0.2-0.3	3901
0.3-0.4	2022
0.4-0.5	613
0.5-0.6	254
0.6-0.7	156
0.7-0.8	25
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7955	Intermediate Similarity	NPD7319	Approved
0.7786	Intermediate Similarity	NPD7492	Approved
0.7752	Intermediate Similarity	NPD6054	Approved
0.7744	Intermediate Similarity	NPD7736	Approved
0.7727	Intermediate Similarity	NPD7507	Approved
0.7727	Intermediate Similarity	NPD6616	Approved
0.7724	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7078	Approved
0.7669	Intermediate Similarity	NPD8293	Discontinued
0.7642	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7634	Intermediate Similarity	NPD6370	Approved
0.7615	Intermediate Similarity	NPD6059	Approved
0.7557	Intermediate Similarity	NPD8517	Approved
0.7557	Intermediate Similarity	NPD8515	Approved
0.7557	Intermediate Similarity	NPD6016	Approved
0.7557	Intermediate Similarity	NPD8513	Phase 3
0.7557	Intermediate Similarity	NPD8516	Approved
0.7557	Intermediate Similarity	NPD6015	Approved
0.7538	Intermediate Similarity	NPD7516	Approved
0.75	Intermediate Similarity	NPD5988	Approved
0.7481	Intermediate Similarity	NPD6319	Approved
0.7462	Intermediate Similarity	NPD7328	Approved
0.7462	Intermediate Similarity	NPD7327	Approved
0.7385	Intermediate Similarity	NPD7115	Discovery
0.7344	Intermediate Similarity	NPD6882	Approved
0.7344	Intermediate Similarity	NPD8297	Approved
0.7293	Intermediate Similarity	NPD8378	Approved
0.7293	Intermediate Similarity	NPD8033	Approved
0.7293	Intermediate Similarity	NPD8296	Approved
0.7293	Intermediate Similarity	NPD8335	Approved
0.7293	Intermediate Similarity	NPD8380	Approved
0.7293	Intermediate Similarity	NPD8379	Approved
0.7279	Intermediate Similarity	NPD8074	Phase 3
0.7266	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD6009	Approved
0.7218	Intermediate Similarity	NPD8377	Approved
0.7218	Intermediate Similarity	NPD8294	Approved
0.7185	Intermediate Similarity	NPD8328	Phase 3
0.7164	Intermediate Similarity	NPD6921	Approved
0.7154	Intermediate Similarity	NPD4632	Approved
0.7143	Intermediate Similarity	NPD6008	Approved
0.7132	Intermediate Similarity	NPD6649	Approved
0.7132	Intermediate Similarity	NPD6650	Approved
0.7121	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6372	Approved
0.7109	Intermediate Similarity	NPD6373	Approved
0.7101	Intermediate Similarity	NPD6033	Approved
0.7077	Intermediate Similarity	NPD6053	Discontinued
0.7054	Intermediate Similarity	NPD6371	Approved
0.7031	Intermediate Similarity	NPD6899	Approved
0.7031	Intermediate Similarity	NPD6881	Approved
0.7031	Intermediate Similarity	NPD7320	Approved
0.7023	Intermediate Similarity	NPD8133	Approved
0.7008	Intermediate Similarity	NPD6402	Approved
0.7008	Intermediate Similarity	NPD5739	Approved
0.7008	Intermediate Similarity	NPD6675	Approved
0.7008	Intermediate Similarity	NPD7128	Approved
0.7	Intermediate Similarity	NPD8130	Phase 1
0.6977	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.696	Remote Similarity	NPD1700	Approved
0.696	Remote Similarity	NPD5344	Discontinued
0.6953	Remote Similarity	NPD5697	Approved
0.6934	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7290	Approved
0.6923	Remote Similarity	NPD4634	Approved
0.6923	Remote Similarity	NPD7102	Approved
0.6923	Remote Similarity	NPD6883	Approved
0.6912	Remote Similarity	NPD7503	Approved
0.6899	Remote Similarity	NPD6686	Approved
0.687	Remote Similarity	NPD6847	Approved
0.687	Remote Similarity	NPD6617	Approved
0.687	Remote Similarity	NPD6869	Approved
0.6846	Remote Similarity	NPD6013	Approved
0.6846	Remote Similarity	NPD6014	Approved
0.6846	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD6012	Approved
0.6822	Remote Similarity	NPD6412	Phase 2
0.6822	Remote Similarity	NPD5701	Approved
0.6788	Remote Similarity	NPD5983	Phase 2
0.6777	Remote Similarity	NPD46	Approved
0.6777	Remote Similarity	NPD6698	Approved
0.6769	Remote Similarity	NPD6011	Approved
0.6721	Remote Similarity	NPD7983	Approved
0.6714	Remote Similarity	NPD6336	Discontinued
0.6712	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6641	Remote Similarity	NPD5211	Phase 2
0.6617	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5285	Approved
0.6614	Remote Similarity	NPD7640	Approved
0.6614	Remote Similarity	NPD5286	Approved
0.6614	Remote Similarity	NPD4696	Approved
0.6614	Remote Similarity	NPD6648	Approved
0.6614	Remote Similarity	NPD7639	Approved
0.6587	Remote Similarity	NPD4755	Approved
0.656	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD1695	Approved
0.6552	Remote Similarity	NPD8338	Approved
0.6547	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5141	Approved
0.6538	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5778	Approved
0.6532	Remote Similarity	NPD5779	Approved
0.6528	Remote Similarity	NPD5956	Approved
0.6527	Remote Similarity	NPD7799	Discontinued
0.6522	Remote Similarity	NPD7100	Approved
0.6522	Remote Similarity	NPD7101	Approved
0.6512	Remote Similarity	NPD5225	Approved
0.6512	Remote Similarity	NPD5226	Approved
0.6512	Remote Similarity	NPD4633	Approved
0.6512	Remote Similarity	NPD5224	Approved
0.6484	Remote Similarity	NPD4700	Approved
0.6483	Remote Similarity	NPD7260	Phase 2
0.6479	Remote Similarity	NPD8451	Approved
0.6463	Remote Similarity	NPD8415	Approved
0.6462	Remote Similarity	NPD5175	Approved
0.6462	Remote Similarity	NPD5174	Approved
0.6457	Remote Similarity	NPD6084	Phase 2
0.6457	Remote Similarity	NPD6083	Phase 2
0.6454	Remote Similarity	NPD7830	Approved
0.6454	Remote Similarity	NPD7829	Approved
0.6454	Remote Similarity	NPD7642	Approved
0.6449	Remote Similarity	NPD6335	Approved
0.6446	Remote Similarity	NPD5786	Approved
0.6434	Remote Similarity	NPD8448	Approved
0.6434	Remote Similarity	NPD5223	Approved
0.6423	Remote Similarity	NPD6274	Approved
0.6419	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6399	Phase 3
0.6391	Remote Similarity	NPD4729	Approved
0.6391	Remote Similarity	NPD4730	Approved
0.6378	Remote Similarity	NPD7839	Suspended
0.6377	Remote Similarity	NPD6317	Approved
0.6371	Remote Similarity	NPD7838	Discovery
0.6364	Remote Similarity	NPD4767	Approved
0.6364	Remote Similarity	NPD4768	Approved
0.6349	Remote Similarity	NPD5282	Discontinued
0.6338	Remote Similarity	NPD6067	Discontinued
0.6331	Remote Similarity	NPD6313	Approved
0.6331	Remote Similarity	NPD6314	Approved
0.6327	Remote Similarity	NPD6845	Suspended
0.6322	Remote Similarity	NPD8055	Clinical (unspecified phase)
0.632	Remote Similarity	NPD7637	Suspended
0.6312	Remote Similarity	NPD6909	Approved
0.6312	Remote Similarity	NPD8444	Approved
0.6312	Remote Similarity	NPD6908	Approved
0.6303	Remote Similarity	NPD5369	Approved
0.6301	Remote Similarity	NPD8390	Approved
0.6301	Remote Similarity	NPD8391	Approved
0.6301	Remote Similarity	NPD8392	Approved
0.6299	Remote Similarity	NPD5695	Phase 3
0.6299	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD5250	Approved
0.6296	Remote Similarity	NPD5251	Approved
0.6296	Remote Similarity	NPD5247	Approved
0.6294	Remote Similarity	NPD8342	Approved
0.6294	Remote Similarity	NPD8299	Approved
0.6294	Remote Similarity	NPD8341	Approved
0.6294	Remote Similarity	NPD8340	Approved
0.629	Remote Similarity	NPD6101	Approved
0.629	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD5696	Approved
0.626	Remote Similarity	NPD4250	Approved
0.626	Remote Similarity	NPD4251	Approved
0.625	Remote Similarity	NPD4269	Approved
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD4270	Approved
0.625	Remote Similarity	NPD8273	Phase 1
0.624	Remote Similarity	NPD5785	Approved
0.6212	Remote Similarity	NPD4754	Approved
0.6198	Remote Similarity	NPD5362	Discontinued
0.6197	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6197	Remote Similarity	NPD8269	Approved
0.6197	Remote Similarity	NPD8268	Approved
0.6197	Remote Similarity	NPD8267	Approved
0.6197	Remote Similarity	NPD8266	Approved
0.619	Remote Similarity	NPD6411	Approved
0.6179	Remote Similarity	NPD4249	Approved
0.6171	Remote Similarity	NPD8407	Phase 2
0.6164	Remote Similarity	NPD8337	Approved
0.6164	Remote Similarity	NPD8336	Approved
0.6154	Remote Similarity	NPD8080	Discontinued
0.6148	Remote Similarity	NPD5128	Approved
0.6136	Remote Similarity	NPD7632	Discontinued
0.6131	Remote Similarity	NPD5215	Approved
0.6131	Remote Similarity	NPD5216	Approved
0.6131	Remote Similarity	NPD5217	Approved
0.6124	Remote Similarity	NPD4697	Phase 3
0.6124	Remote Similarity	NPD5221	Approved
0.6124	Remote Similarity	NPD5222	Approved
0.6124	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6118	Remote Similarity	NPD6334	Approved
0.6118	Remote Similarity	NPD6333	Approved
0.6098	Remote Similarity	NPD6082	Clinical (unspecified phase)

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