NPASS Compound

Structure

CID317671 OpenBabel06191716142D 67 75 0 0 1 0 0 0 0 0999 V2000 1.7593 -3.8914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1364 -0.1926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1268 0.3731 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1455 -1.1783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8530 -2.9100 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2827 -0.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2731 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5623 -4.4632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9901 -0.6855 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9806 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1323 -0.2325 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 2.7497 -2.5005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2827 -1.6712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2731 1.8518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7402 2.6811 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4624 2.5543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6932 1.7684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 3.0906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4624 0.9826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 0.4462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4590 -4.0537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9901 -1.6712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9806 1.8518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5527 -3.0723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1364 -2.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1268 2.3447 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6669 2.8414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3892 2.7146 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0354 2.0062 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3539 0.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0328 0.3297 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4915 2.8582 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4393 1.6401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8773 0.4131 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.7122 0.6699 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.1550 1.3589 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8773 -2.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7402 0.0367 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7497 0.1438 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1323 2.9503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9678 0.1392 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4686 -5.4445 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8438 -0.1926 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8343 0.3731 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2620 -4.6255 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.8438 -2.1641 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.8343 2.3447 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4494 -2.6628 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1364 -3.1499 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1268 3.3305 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2388 3.6444 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4079 2.8083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 2.9868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5798 0.6298 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.2478 -1.6218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0820 3.7549 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3899 2.1730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4678 -3.6665 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3857 -0.7083 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.3953 0.8888 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5418 3.8470 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5176 -0.6791 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1323 -2.1242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8435 -0.3728 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8530 0.5534 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 0.8773 2.3048 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 1 8 1 0 0 0 0 2 6 2 0 0 0 0 2 9 1 0 0 0 0 3 7 2 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 4 63 1 0 0 0 0 5 12 1 0 0 0 0 5 37 1 0 0 0 0 6 13 1 0 0 0 0 6 39 1 0 0 0 0 7 14 1 0 0 0 0 7 38 1 0 0 0 0 8 21 2 0 0 0 0 8 42 1 0 0 0 0 9 22 2 0 0 0 0 9 43 1 0 0 0 0 10 23 2 0 0 0 0 10 44 1 0 0 0 0 11 34 1 0 0 0 0 11 64 1 0 0 0 0 12 13 1 0 0 0 0 12 24 2 0 0 0 0 13 25 2 0 0 0 0 14 15 1 0 0 0 0 14 26 2 0 0 0 0 15 18 2 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 18 1 0 0 0 0 16 28 2 0 0 0 0 17 19 2 0 0 0 0 17 29 1 0 0 0 0 18 40 1 0 0 0 0 19 20 1 0 0 0 0 19 41 1 0 0 0 0 20 30 2 0 0 0 0 20 31 1 0 0 0 0 21 24 1 0 0 0 0 21 45 1 0 0 0 0 22 25 1 0 0 0 0 22 46 1 0 0 0 0 23 26 1 0 0 0 0 23 47 1 0 0 0 0 24 48 1 0 0 0 0 25 49 1 0 0 0 0 26 50 1 0 0 0 0 27 32 2 0 0 0 0 27 51 1 0 0 0 0 28 32 1 0 0 0 0 28 52 1 0 0 0 0 29 33 2 0 0 0 0 29 53 1 0 0 0 0 30 33 1 0 0 0 0 30 54 1 0 0 0 0 31 35 1 0 0 0 0 31 55 1 1 0 0 0 32 56 1 0 0 0 0 33 57 1 0 0 0 0 34 36 1 0 0 0 0 34 65 1 0 0 0 0 35 36 1 0 0 0 0 35 66 1 0 0 0 0 36 67 1 0 0 0 0 37 58 2 0 0 0 0 37 63 1 0 0 0 0 38 59 2 0 0 0 0 38 64 1 0 0 0 0 39 60 2 0 0 0 0 39 65 1 0 0 0 0 40 61 2 0 0 0 0 40 67 1 0 0 0 0 41 62 2 0 0 0 0 41 66 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	934.07
Volume:	816.5
LogP:	1.707
LogD:	0.99
LogS:	-3.928
# Rotatable Bonds:	0
TPSA:	455.18
# H-Bond Aceptor:	26
# H-Bond Donor:	16
# Rings:	10
# Heavy Atoms:	26

MedChem Properties

QED Drug-Likeness Score:	0.059
Synthetic Accessibility Score:	7.068
Fsp3:	0.146
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-7.207
MDCK Permeability:	3.2334805837308522e-06
Pgp-inhibitor:	0.308
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	1.0
20% Bioavailability (F20%):	0.895
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0
Plasma Protein Binding (PPB):	87.11717987060547%
Volume Distribution (VD):	0.312
Pgp-substrate:	63.46529769897461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.002
CYP2C19-inhibitor:	0.003
CYP2C19-substrate:	0.019
CYP2C9-inhibitor:	0.172
CYP2C9-substrate:	0.013
CYP2D6-inhibitor:	0.0
CYP2D6-substrate:	0.051
CYP3A4-inhibitor:	0.002
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	7.869
Half-life (T1/2):	0.917

ADMET: Toxicity

hERG Blockers:	0.015
Human Hepatotoxicity (H-HT):	0.031
Drug-inuced Liver Injury (DILI):	0.996
AMES Toxicity:	0.057
Rat Oral Acute Toxicity:	0.0
Maximum Recommended Daily Dose:	0.012
Skin Sensitization:	0.936
Carcinogencity:	0.002
Eye Corrosion:	0.003
Eye Irritation:	0.918
Respiratory Toxicity:	0.0

Download Data

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

Natural Product: NPC317671

Natural Product ID:	NPC317671
*Common Name:**	UDYKDZHZAKSYCO-KCPYMCPDSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UDYKDZHZAKSYCO-KCPYMCPDSA-N
Standard InCHI:	InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11?,31-,34?,35?,36?/m0/s1
SMILES:	C1C2C(C3C4C(C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL288949
PubChem CID:	3002102
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000238] Tannins [CHEMONTID:0001710] Hydrolyzable tannins

*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
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1191	Castanea mollissima	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1191	Castanea mollissima	Species	Fagaceae	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
EC50	1
IC50	2
Others	4

Activity Type	# Activity
Individual Protein	1
Organism	3
Others	1
Protein Family	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT459	Individual Protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	Inhibition	=	40.0	%	PMID[524213]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	IC50	=	15000.0	nM	PMID[524213]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	15000.0	nM	PMID[524213]
NPT27	Others	Unspecified		Therapeutic index	=	1.0	n.a.	PMID[524213]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	Inhibition	=	90.0	%	PMID[524213]
NPT316	Protein Family	Protein kinase C (PKC)	Homo sapiens	IC50	=	4000.0	nM	PMID[524214]
NPT727	Protein Family	Protein kinase C, PKC; classical/novel	Homo sapiens	Phorbol displacement	<=	50.0	uM	PMID[524214]

☑ 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 NPC317671 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	407
0.1-0.2	1710
0.2-0.3	3951
0.3-0.4	9238
0.4-0.5	9402
0.5-0.6	4472
0.6-0.7	6698
0.7-0.8	6431
0.8-0.85	311
0.85-0.9	54
0.9-0.95	14
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC26536
1.0	High Similarity	NPC49983
1.0	High Similarity	NPC142707
0.9936	High Similarity	NPC162169
0.9936	High Similarity	NPC166851
0.9936	High Similarity	NPC217781
0.9563	High Similarity	NPC31034
0.9444	High Similarity	NPC47521
0.9398	High Similarity	NPC125352
0.9379	High Similarity	NPC175793
0.9321	High Similarity	NPC190204
0.9321	High Similarity	NPC261411
0.9321	High Similarity	NPC470271
0.9321	High Similarity	NPC311389
0.9321	High Similarity	NPC43918
0.9207	High Similarity	NPC470272
0.9176	High Similarity	NPC237202
0.9152	High Similarity	NPC65333
0.9123	High Similarity	NPC269046
0.9074	High Similarity	NPC14030
0.9074	High Similarity	NPC291957
0.9062	High Similarity	NPC474010
0.9062	High Similarity	NPC135222
0.9036	High Similarity	NPC100251
0.9018	High Similarity	NPC470898
0.9	High Similarity	NPC123259
0.9	High Similarity	NPC129533
0.8988	High Similarity	NPC472723
0.8982	High Similarity	NPC98583
0.8882	High Similarity	NPC239019
0.8882	High Similarity	NPC247629
0.8882	High Similarity	NPC80956
0.8854	High Similarity	NPC142528
0.883	High Similarity	NPC8940
0.8827	High Similarity	NPC238419
0.8827	High Similarity	NPC172419
0.879	High Similarity	NPC268366
0.8786	High Similarity	NPC112380
0.8786	High Similarity	NPC469650
0.878	High Similarity	NPC266365
0.8773	High Similarity	NPC318826
0.8773	High Similarity	NPC210501
0.8773	High Similarity	NPC114791
0.8773	High Similarity	NPC141331
0.8773	High Similarity	NPC104222
0.8765	High Similarity	NPC134925
0.8736	High Similarity	NPC65489
0.8728	High Similarity	NPC231254
0.872	High Similarity	NPC24627
0.8704	High Similarity	NPC203757
0.8701	High Similarity	NPC477082
0.8693	High Similarity	NPC264302
0.8693	High Similarity	NPC40078
0.8693	High Similarity	NPC471091
0.8693	High Similarity	NPC97924
0.8678	High Similarity	NPC111490
0.8678	High Similarity	NPC261623
0.8655	High Similarity	NPC297574
0.865	High Similarity	NPC250436
0.865	High Similarity	NPC88803
0.865	High Similarity	NPC291948
0.865	High Similarity	NPC104983
0.865	High Similarity	NPC300845
0.8636	High Similarity	NPC469652
0.8636	High Similarity	NPC472721
0.8636	High Similarity	NPC93065
0.8636	High Similarity	NPC472724
0.8636	High Similarity	NPC160543
0.8636	High Similarity	NPC31208
0.8636	High Similarity	NPC472720
0.8631	High Similarity	NPC107009
0.8629	High Similarity	NPC260521
0.8629	High Similarity	NPC469649
0.8629	High Similarity	NPC269625
0.8623	High Similarity	NPC471788
0.8613	High Similarity	NPC208797
0.8613	High Similarity	NPC117668
0.8613	High Similarity	NPC53680
0.8611	High Similarity	NPC174140
0.8606	High Similarity	NPC24164
0.8605	High Similarity	NPC471789
0.8605	High Similarity	NPC265380
0.8599	High Similarity	NPC22176
0.8599	High Similarity	NPC190587
0.8599	High Similarity	NPC121573
0.8599	High Similarity	NPC226738
0.8598	High Similarity	NPC289322
0.8598	High Similarity	NPC160512
0.8598	High Similarity	NPC38779
0.8598	High Similarity	NPC68324
0.8598	High Similarity	NPC114179
0.8598	High Similarity	NPC156818
0.8596	High Similarity	NPC476358
0.858	High Similarity	NPC61152
0.858	High Similarity	NPC477081
0.858	High Similarity	NPC173872
0.858	High Similarity	NPC240200
0.858	High Similarity	NPC477083
0.858	High Similarity	NPC16024
0.858	High Similarity	NPC3746
0.858	High Similarity	NPC119094
0.858	High Similarity	NPC205037
0.858	High Similarity	NPC223534
0.858	High Similarity	NPC44260
0.858	High Similarity	NPC290289
0.858	High Similarity	NPC158214
0.8571	High Similarity	NPC252979
0.8555	High Similarity	NPC198902
0.8555	High Similarity	NPC185275
0.8547	High Similarity	NPC67629
0.8547	High Similarity	NPC79736
0.8545	High Similarity	NPC87317
0.8545	High Similarity	NPC471750
0.8537	High Similarity	NPC318432
0.8531	High Similarity	NPC187632
0.8529	High Similarity	NPC180768
0.8528	High Similarity	NPC238672
0.8528	High Similarity	NPC144801
0.8528	High Similarity	NPC197188
0.8528	High Similarity	NPC43872
0.8528	High Similarity	NPC291510
0.8528	High Similarity	NPC116850
0.8521	High Similarity	NPC473818
0.8519	High Similarity	NPC227485
0.8503	High Similarity	NPC476371
0.8503	High Similarity	NPC476372
0.85	High Similarity	NPC81835
0.85	High Similarity	NPC189312
0.8497	Intermediate Similarity	NPC267549
0.8494	Intermediate Similarity	NPC53889
0.848	Intermediate Similarity	NPC212038
0.848	Intermediate Similarity	NPC477836
0.848	Intermediate Similarity	NPC271848
0.848	Intermediate Similarity	NPC289396
0.848	Intermediate Similarity	NPC262580
0.848	Intermediate Similarity	NPC81332
0.8475	Intermediate Similarity	NPC7839
0.8475	Intermediate Similarity	NPC142291
0.8462	Intermediate Similarity	NPC477835
0.8462	Intermediate Similarity	NPC9309
0.8452	Intermediate Similarity	NPC67959
0.8448	Intermediate Similarity	NPC324742
0.8443	Intermediate Similarity	NPC139540
0.8443	Intermediate Similarity	NPC177100
0.8434	Intermediate Similarity	NPC40702
0.8434	Intermediate Similarity	NPC37502
0.8434	Intermediate Similarity	NPC267627
0.843	Intermediate Similarity	NPC34436
0.843	Intermediate Similarity	NPC166674
0.843	Intermediate Similarity	NPC46640
0.843	Intermediate Similarity	NPC263119
0.843	Intermediate Similarity	NPC219600
0.843	Intermediate Similarity	NPC473550
0.8427	Intermediate Similarity	NPC201814
0.8421	Intermediate Similarity	NPC181778
0.8421	Intermediate Similarity	NPC476365
0.8418	Intermediate Similarity	NPC105591
0.8415	Intermediate Similarity	NPC125487
0.8415	Intermediate Similarity	NPC281703
0.8405	Intermediate Similarity	NPC228662
0.8393	Intermediate Similarity	NPC473445
0.8385	Intermediate Similarity	NPC43123
0.8385	Intermediate Similarity	NPC120621
0.8385	Intermediate Similarity	NPC476463
0.8385	Intermediate Similarity	NPC248257
0.8383	Intermediate Similarity	NPC476373
0.8373	Intermediate Similarity	NPC247713
0.8372	Intermediate Similarity	NPC186847
0.8372	Intermediate Similarity	NPC4200
0.8372	Intermediate Similarity	NPC472454
0.8372	Intermediate Similarity	NPC257667
0.8363	Intermediate Similarity	NPC198125
0.8363	Intermediate Similarity	NPC149300
0.8363	Intermediate Similarity	NPC300307
0.8363	Intermediate Similarity	NPC475212
0.8363	Intermediate Similarity	NPC95421
0.8354	Intermediate Similarity	NPC474656
0.8353	Intermediate Similarity	NPC171985
0.8353	Intermediate Similarity	NPC207575
0.8353	Intermediate Similarity	NPC13481
0.8353	Intermediate Similarity	NPC224851
0.8353	Intermediate Similarity	NPC320741
0.8352	Intermediate Similarity	NPC132111
0.8344	Intermediate Similarity	NPC225036
0.8344	Intermediate Similarity	NPC12218
0.8344	Intermediate Similarity	NPC75763
0.8344	Intermediate Similarity	NPC105525
0.8344	Intermediate Similarity	NPC140151
0.8343	Intermediate Similarity	NPC45943
0.8343	Intermediate Similarity	NPC291977
0.8343	Intermediate Similarity	NPC469651
0.8333	Intermediate Similarity	NPC92117
0.8333	Intermediate Similarity	NPC42464
0.8333	Intermediate Similarity	NPC221352
0.8323	Intermediate Similarity	NPC7543
0.8323	Intermediate Similarity	NPC98083
0.8323	Intermediate Similarity	NPC94220
0.8323	Intermediate Similarity	NPC24339
0.8323	Intermediate Similarity	NPC166456
0.8315	Intermediate Similarity	NPC179947

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 NPC317671 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	364
0.1-0.2	964
0.2-0.3	1961
0.3-0.4	2813
0.4-0.5	1782
0.5-0.6	913
0.6-0.7	255
0.7-0.8	94
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8698	High Similarity	NPD7993	Clinical (unspecified phase)
0.865	High Similarity	NPD4868	Clinical (unspecified phase)
0.8363	Intermediate Similarity	NPD5844	Phase 1
0.8303	Intermediate Similarity	NPD1465	Phase 2
0.8176	Intermediate Similarity	NPD6232	Discontinued
0.8118	Intermediate Similarity	NPD6959	Discontinued
0.8101	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8035	Intermediate Similarity	NPD7473	Discontinued
0.7977	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7977	Intermediate Similarity	NPD6166	Phase 2
0.7977	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7921	Intermediate Similarity	NPD8312	Approved
0.7921	Intermediate Similarity	NPD8313	Approved
0.7904	Intermediate Similarity	NPD4380	Phase 2
0.7874	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.787	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD7390	Discontinued
0.7853	Intermediate Similarity	NPD8151	Discontinued
0.7853	Intermediate Similarity	NPD6190	Approved
0.7848	Intermediate Similarity	NPD230	Phase 1
0.7784	Intermediate Similarity	NPD7228	Approved
0.7765	Intermediate Similarity	NPD7819	Suspended
0.7717	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD1934	Approved
0.7697	Intermediate Similarity	NPD7472	Approved
0.7697	Intermediate Similarity	NPD7074	Phase 3
0.7692	Intermediate Similarity	NPD8150	Discontinued
0.7688	Intermediate Similarity	NPD6234	Discontinued
0.7684	Intermediate Similarity	NPD3818	Discontinued
0.7674	Intermediate Similarity	NPD7768	Phase 2
0.7667	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD8455	Phase 2
0.7654	Intermediate Similarity	NPD6797	Phase 2
0.764	Intermediate Similarity	NPD7054	Approved
0.763	Intermediate Similarity	NPD7075	Discontinued
0.7611	Intermediate Similarity	NPD7251	Discontinued
0.7602	Intermediate Similarity	NPD37	Approved
0.7572	Intermediate Similarity	NPD4966	Approved
0.7572	Intermediate Similarity	NPD4965	Approved
0.7572	Intermediate Similarity	NPD4967	Phase 2
0.7569	Intermediate Similarity	NPD7808	Phase 3
0.7546	Intermediate Similarity	NPD5406	Approved
0.7546	Intermediate Similarity	NPD5405	Approved
0.7546	Intermediate Similarity	NPD5404	Approved
0.7546	Intermediate Similarity	NPD5408	Approved
0.7544	Intermediate Similarity	NPD7411	Suspended
0.7541	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3749	Approved
0.7514	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6801	Discontinued
0.747	Intermediate Similarity	NPD8166	Discontinued
0.7457	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD2801	Approved
0.7444	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7443	Intermediate Similarity	NPD5494	Approved
0.7427	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7418	Intermediate Similarity	NPD6559	Discontinued
0.7418	Intermediate Similarity	NPD7240	Approved
0.7414	Intermediate Similarity	NPD3817	Phase 2
0.7401	Intermediate Similarity	NPD7199	Phase 2
0.7396	Intermediate Similarity	NPD2533	Approved
0.7396	Intermediate Similarity	NPD2532	Approved
0.7396	Intermediate Similarity	NPD2534	Approved
0.7371	Intermediate Similarity	NPD3882	Suspended
0.7365	Intermediate Similarity	NPD3750	Approved
0.7346	Intermediate Similarity	NPD943	Approved
0.7337	Intermediate Similarity	NPD1511	Approved
0.7329	Intermediate Similarity	NPD3764	Approved
0.7322	Intermediate Similarity	NPD7685	Pre-registration
0.7314	Intermediate Similarity	NPD5402	Approved
0.731	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD3751	Discontinued
0.7289	Intermediate Similarity	NPD7266	Discontinued
0.7282	Intermediate Similarity	NPD8320	Phase 1
0.7282	Intermediate Similarity	NPD8319	Approved
0.7273	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD3787	Discontinued
0.7263	Intermediate Similarity	NPD6535	Approved
0.7263	Intermediate Similarity	NPD6534	Approved
0.7262	Intermediate Similarity	NPD7003	Approved
0.7261	Intermediate Similarity	NPD9269	Phase 2
0.7251	Intermediate Similarity	NPD1512	Approved
0.7246	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD7700	Phase 2
0.724	Intermediate Similarity	NPD7699	Phase 2
0.7231	Intermediate Similarity	NPD7435	Discontinued
0.7222	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7194	Intermediate Similarity	NPD7871	Phase 2
0.7194	Intermediate Similarity	NPD7870	Phase 2
0.7193	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7165	Intermediate Similarity	NPD6779	Approved
0.7165	Intermediate Similarity	NPD6778	Approved
0.7165	Intermediate Similarity	NPD6776	Approved
0.7165	Intermediate Similarity	NPD6777	Approved
0.7165	Intermediate Similarity	NPD6780	Approved
0.7165	Intermediate Similarity	NPD6782	Approved
0.7165	Intermediate Similarity	NPD6781	Approved
0.716	Intermediate Similarity	NPD4628	Phase 3
0.715	Intermediate Similarity	NPD7783	Phase 2
0.715	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1549	Phase 2
0.7134	Intermediate Similarity	NPD1613	Approved
0.7134	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7458	Discontinued
0.711	Intermediate Similarity	NPD5403	Approved
0.71	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD7874	Approved
0.7093	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7229	Phase 3
0.7069	Intermediate Similarity	NPD1653	Approved
0.7066	Intermediate Similarity	NPD1510	Phase 2
0.7066	Intermediate Similarity	NPD3748	Approved
0.7056	Intermediate Similarity	NPD7697	Approved
0.7056	Intermediate Similarity	NPD7696	Phase 3
0.7056	Intermediate Similarity	NPD7680	Approved
0.7056	Intermediate Similarity	NPD7698	Approved
0.7035	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7035	Intermediate Similarity	NPD6799	Approved
0.7031	Intermediate Similarity	NPD6213	Phase 3
0.7031	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD6212	Phase 3
0.7029	Intermediate Similarity	NPD3226	Approved
0.7026	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2935	Discontinued
0.7017	Intermediate Similarity	NPD8127	Discontinued
0.7011	Intermediate Similarity	NPD7177	Discontinued
0.7006	Intermediate Similarity	NPD9268	Approved
0.7	Intermediate Similarity	NPD7701	Phase 2
0.6994	Remote Similarity	NPD5401	Approved
0.6989	Remote Similarity	NPD6599	Discontinued
0.6978	Remote Similarity	NPD5711	Approved
0.6978	Remote Similarity	NPD5710	Approved
0.6951	Remote Similarity	NPD3027	Phase 3
0.6947	Remote Similarity	NPD8434	Phase 2
0.6933	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8155	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8090	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6823	Phase 2
0.6906	Remote Similarity	NPD919	Approved
0.6897	Remote Similarity	NPD7801	Approved
0.689	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.686	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD6273	Approved
0.6848	Remote Similarity	NPD3926	Phase 2
0.6848	Remote Similarity	NPD5242	Approved
0.6833	Remote Similarity	NPD5353	Approved
0.6826	Remote Similarity	NPD1240	Approved
0.6824	Remote Similarity	NPD2796	Approved
0.6818	Remote Similarity	NPD920	Approved
0.6818	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD2346	Discontinued
0.6754	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6746	Remote Similarity	NPD1607	Approved
0.6742	Remote Similarity	NPD3455	Phase 2
0.6739	Remote Similarity	NPD1247	Approved
0.6733	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.673	Remote Similarity	NPD9545	Approved
0.6725	Remote Similarity	NPD1551	Phase 2
0.672	Remote Similarity	NPD5953	Discontinued
0.6707	Remote Similarity	NPD1470	Approved
0.6705	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2800	Approved
0.6705	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6702	Remote Similarity	NPD7286	Phase 2
0.6701	Remote Similarity	NPD4287	Approved
0.6687	Remote Similarity	NPD4908	Phase 1
0.6667	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD7549	Discontinued
0.6648	Remote Similarity	NPD4288	Approved
0.6647	Remote Similarity	NPD7008	Discontinued
0.6628	Remote Similarity	NPD6100	Approved
0.6628	Remote Similarity	NPD2438	Suspended
0.6628	Remote Similarity	NPD6099	Approved
0.6627	Remote Similarity	NPD4060	Phase 1
0.6627	Remote Similarity	NPD9494	Approved
0.6609	Remote Similarity	NPD1243	Approved
0.6609	Remote Similarity	NPD6674	Discontinued
0.6607	Remote Similarity	NPD6798	Discontinued
0.6606	Remote Similarity	NPD1164	Approved
0.6591	Remote Similarity	NPD643	Clinical (unspecified phase)
0.659	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD447	Suspended
0.6588	Remote Similarity	NPD5124	Phase 1
0.6588	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD7585	Approved
0.6575	Remote Similarity	NPD6385	Approved
0.6575	Remote Similarity	NPD6386	Approved
0.657	Remote Similarity	NPD2799	Discontinued
0.6564	Remote Similarity	NPD1201	Approved
0.6555	Remote Similarity	NPD7930	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