NPASS Compound

Structure

CID318067 OpenBabel06191716142D 41 43 0 0 1 0 0 0 0 0999 V2000 -13.8564 8.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 7.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -14.7224 6.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -13.8564 5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.9904 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -12.1244 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -11.2583 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -10.3923 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5263 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 26 1 0 0 0 0 3 27 1 0 0 0 0 4 5 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 2 0 0 0 0 12 13 1 0 0 0 0 13 14 1 0 0 0 0 14 15 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 18 1 0 0 0 0 18 22 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 26 1 0 0 0 0 21 29 2 0 0 0 0 22 31 1 0 0 0 0 23 24 2 0 0 0 0 23 28 1 0 0 0 0 24 30 1 0 0 0 0 25 27 1 0 0 0 0 25 41 1 0 0 0 0 26 28 2 0 0 0 0 27 32 1 0 0 0 0 28 29 1 0 0 0 0 29 33 1 0 0 0 0 30 33 2 0 0 0 0 30 34 1 0 0 0 0 31 37 2 0 0 0 0 31 41 1 0 0 0 0 32 34 1 0 0 0 0 32 35 2 0 0 0 0 33 36 1 0 0 0 0 34 38 2 0 0 0 0 35 36 1 0 0 0 0 35 39 1 0 0 0 0 36 40 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.35
Volume:	623.129
LogP:	9.323
LogD:	5.229
LogS:	-2.52
# Rotatable Bonds:	18
TPSA:	86.99
# H-Bond Aceptor:	5
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.029
Synthetic Accessibility Score:	3.15
Fsp3:	0.472
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.016
MDCK Permeability:	1.2778801647073124e-05
Pgp-inhibitor:	0.431
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	101.96056365966797%
Volume Distribution (VD):	2.547
Pgp-substrate:	0.7819048166275024%

ADMET: Metabolism

CYP1A2-inhibitor:	0.544
CYP1A2-substrate:	0.17
CYP2C19-inhibitor:	0.622
CYP2C19-substrate:	0.062
CYP2C9-inhibitor:	0.179
CYP2C9-substrate:	0.959
CYP2D6-inhibitor:	0.439
CYP2D6-substrate:	0.721
CYP3A4-inhibitor:	0.156
CYP3A4-substrate:	0.054

ADMET: Excretion

Clearance (CL):	2.425
Half-life (T1/2):	0.479

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.085
Drug-inuced Liver Injury (DILI):	0.301
AMES Toxicity:	0.377
Rat Oral Acute Toxicity:	0.077
Maximum Recommended Daily Dose:	0.59
Skin Sensitization:	0.973
Carcinogencity:	0.337
Eye Corrosion:	0.003
Eye Irritation:	0.896
Respiratory Toxicity:	0.706

Download Data

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

Natural Product: NPC318067

Natural Product ID:	NPC318067
*Common Name:**	16-O-Oleoyl Danshenxinkun A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	CKCNLHQWTDJDRS-QXMHVHEDSA-N
Standard InCHI:	InChI=1S/C36H48O5/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22-31(37)41-25-27(3)32-34(38)30-24-23-28-26(2)20-19-21-29(28)33(30)36(40)35(32)39/h11-12,19-21,23-24,27,39H,4-10,13-18,22,25H2,1-3H3/b12-11-
SMILES:	CCCCCCCC/C=CCCCCCCCC(=O)OCC(C1=C(O)C(=O)c2c(C1=O)ccc1c2cccc1C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL473262
PubChem CID:	NA
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[11374966]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16038550]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17583950]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18855446]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20455578]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21775156]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23286284]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24108414]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27569393]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29185738]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30351923]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[3655791]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	roots	n.a.	n.a.	PMID[9834151]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO5743	Salvia miltiorrhiza	Species	Lamiaceae	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
IC50	3

Activity Type	# Activity
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	25500.0	nM	PMID[556247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	60500.0	nM	PMID[556247]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100000.0	nM	PMID[556247]

☑ 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 NPC318067 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	237
0.1-0.2	1045
0.2-0.3	2158
0.3-0.4	6642
0.4-0.5	13297
0.5-0.6	12432
0.6-0.7	6189
0.7-0.8	641
0.8-0.85	42
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC328107
0.9316	High Similarity	NPC318173
0.8917	High Similarity	NPC202015
0.8908	High Similarity	NPC323440
0.8908	High Similarity	NPC222968
0.8908	High Similarity	NPC80605
0.8718	High Similarity	NPC292834
0.8644	High Similarity	NPC143768
0.864	High Similarity	NPC295664
0.8607	High Similarity	NPC204784
0.8583	High Similarity	NPC51448
0.8583	High Similarity	NPC115797
0.8417	Intermediate Similarity	NPC326664
0.8403	Intermediate Similarity	NPC186128
0.8362	Intermediate Similarity	NPC134120
0.8362	Intermediate Similarity	NPC172483
0.8347	Intermediate Similarity	NPC217111
0.8308	Intermediate Similarity	NPC471832
0.8295	Intermediate Similarity	NPC478162
0.8295	Intermediate Similarity	NPC478165
0.8291	Intermediate Similarity	NPC100767
0.8276	Intermediate Similarity	NPC329282
0.8264	Intermediate Similarity	NPC67377
0.8264	Intermediate Similarity	NPC471721
0.822	Intermediate Similarity	NPC203732
0.8211	Intermediate Similarity	NPC469843
0.819	Intermediate Similarity	NPC329556
0.819	Intermediate Similarity	NPC274443
0.8182	Intermediate Similarity	NPC93287
0.8182	Intermediate Similarity	NPC470253
0.8175	Intermediate Similarity	NPC144547
0.8167	Intermediate Similarity	NPC265513
0.8125	Intermediate Similarity	NPC85511
0.8103	Intermediate Similarity	NPC222390
0.8103	Intermediate Similarity	NPC244427
0.8099	Intermediate Similarity	NPC66208
0.8099	Intermediate Similarity	NPC218855
0.8099	Intermediate Similarity	NPC280789
0.8095	Intermediate Similarity	NPC105709
0.8095	Intermediate Similarity	NPC988
0.8095	Intermediate Similarity	NPC289432
0.8065	Intermediate Similarity	NPC158157
0.8034	Intermediate Similarity	NPC247976
0.8017	Intermediate Similarity	NPC137315
0.8016	Intermediate Similarity	NPC476645
0.8	Intermediate Similarity	NPC61651
0.8	Intermediate Similarity	NPC328997
0.8	Intermediate Similarity	NPC294050
0.7969	Intermediate Similarity	NPC269923
0.7969	Intermediate Similarity	NPC167323
0.7967	Intermediate Similarity	NPC234637
0.7967	Intermediate Similarity	NPC241851
0.7967	Intermediate Similarity	NPC130591
0.7967	Intermediate Similarity	NPC196673
0.7953	Intermediate Similarity	NPC232958
0.7941	Intermediate Similarity	NPC309056
0.7917	Intermediate Similarity	NPC21929
0.7907	Intermediate Similarity	NPC65627
0.7903	Intermediate Similarity	NPC215419
0.7903	Intermediate Similarity	NPC470764
0.7886	Intermediate Similarity	NPC471481
0.7879	Intermediate Similarity	NPC316553
0.7869	Intermediate Similarity	NPC474057
0.7868	Intermediate Similarity	NPC23894
0.7851	Intermediate Similarity	NPC318327
0.7851	Intermediate Similarity	NPC192577
0.7846	Intermediate Similarity	NPC325740
0.7846	Intermediate Similarity	NPC51079
0.7845	Intermediate Similarity	NPC49994
0.784	Intermediate Similarity	NPC135730
0.7836	Intermediate Similarity	NPC27659
0.7833	Intermediate Similarity	NPC142326
0.7833	Intermediate Similarity	NPC94751
0.7833	Intermediate Similarity	NPC37914
0.7823	Intermediate Similarity	NPC294458
0.7812	Intermediate Similarity	NPC77000
0.7812	Intermediate Similarity	NPC238861
0.7803	Intermediate Similarity	NPC146239
0.7794	Intermediate Similarity	NPC203486
0.7778	Intermediate Similarity	NPC105141
0.7778	Intermediate Similarity	NPC242764
0.776	Intermediate Similarity	NPC186933
0.776	Intermediate Similarity	NPC228936
0.776	Intermediate Similarity	NPC474095
0.7759	Intermediate Similarity	NPC156021
0.7752	Intermediate Similarity	NPC472981
0.775	Intermediate Similarity	NPC471186
0.7737	Intermediate Similarity	NPC474659
0.7727	Intermediate Similarity	NPC470765
0.7727	Intermediate Similarity	NPC236405
0.7717	Intermediate Similarity	NPC45794
0.7712	Intermediate Similarity	NPC112552
0.771	Intermediate Similarity	NPC12881
0.771	Intermediate Similarity	NPC140118
0.7698	Intermediate Similarity	NPC260886
0.7686	Intermediate Similarity	NPC185763
0.7686	Intermediate Similarity	NPC83409
0.768	Intermediate Similarity	NPC153053
0.7674	Intermediate Similarity	NPC473243
0.7669	Intermediate Similarity	NPC473220
0.7669	Intermediate Similarity	NPC81135
0.7669	Intermediate Similarity	NPC470753
0.7669	Intermediate Similarity	NPC169913
0.7669	Intermediate Similarity	NPC15837
0.7669	Intermediate Similarity	NPC48992
0.7664	Intermediate Similarity	NPC329913
0.7661	Intermediate Similarity	NPC79496
0.7661	Intermediate Similarity	NPC471189
0.7661	Intermediate Similarity	NPC270699
0.7661	Intermediate Similarity	NPC82899
0.7656	Intermediate Similarity	NPC254233
0.7623	Intermediate Similarity	NPC470391
0.7615	Intermediate Similarity	NPC476234
0.7609	Intermediate Similarity	NPC212207
0.7603	Intermediate Similarity	NPC105899
0.76	Intermediate Similarity	NPC469547
0.76	Intermediate Similarity	NPC477476
0.76	Intermediate Similarity	NPC477475
0.76	Intermediate Similarity	NPC13784
0.7594	Intermediate Similarity	NPC275576
0.7594	Intermediate Similarity	NPC476599
0.7591	Intermediate Similarity	NPC144257
0.7586	Intermediate Similarity	NPC172925
0.7581	Intermediate Similarity	NPC1082
0.7581	Intermediate Similarity	NPC291799
0.7581	Intermediate Similarity	NPC305912
0.7581	Intermediate Similarity	NPC210089
0.7578	Intermediate Similarity	NPC228318
0.7578	Intermediate Similarity	NPC268930
0.7578	Intermediate Similarity	NPC152812
0.7563	Intermediate Similarity	NPC225079
0.7563	Intermediate Similarity	NPC128248
0.7563	Intermediate Similarity	NPC136810
0.7563	Intermediate Similarity	NPC133809
0.7559	Intermediate Similarity	NPC9274
0.7559	Intermediate Similarity	NPC62138
0.7556	Intermediate Similarity	NPC96024
0.7556	Intermediate Similarity	NPC225103
0.7542	Intermediate Similarity	NPC134882
0.7542	Intermediate Similarity	NPC145052
0.7538	Intermediate Similarity	NPC472680
0.7538	Intermediate Similarity	NPC472679
0.7536	Intermediate Similarity	NPC126516
0.7536	Intermediate Similarity	NPC310662
0.7535	Intermediate Similarity	NPC315578
0.7533	Intermediate Similarity	NPC3898
0.752	Intermediate Similarity	NPC321852
0.7519	Intermediate Similarity	NPC164014
0.7518	Intermediate Similarity	NPC472394
0.7517	Intermediate Similarity	NPC478160
0.75	Intermediate Similarity	NPC214067
0.75	Intermediate Similarity	NPC34243
0.75	Intermediate Similarity	NPC478164
0.75	Intermediate Similarity	NPC238219
0.75	Intermediate Similarity	NPC472388
0.75	Intermediate Similarity	NPC93084
0.75	Intermediate Similarity	NPC473443
0.75	Intermediate Similarity	NPC251854
0.75	Intermediate Similarity	NPC212891
0.75	Intermediate Similarity	NPC196246
0.748	Intermediate Similarity	NPC476357
0.748	Intermediate Similarity	NPC112903
0.748	Intermediate Similarity	NPC474408
0.748	Intermediate Similarity	NPC93181
0.748	Intermediate Similarity	NPC221275
0.7479	Intermediate Similarity	NPC476042
0.7479	Intermediate Similarity	NPC221825
0.7465	Intermediate Similarity	NPC470407
0.7465	Intermediate Similarity	NPC26924
0.7465	Intermediate Similarity	NPC213567
0.7464	Intermediate Similarity	NPC58685
0.7462	Intermediate Similarity	NPC472708
0.746	Intermediate Similarity	NPC128368
0.7458	Intermediate Similarity	NPC265220
0.7458	Intermediate Similarity	NPC226041
0.7458	Intermediate Similarity	NPC239185
0.7458	Intermediate Similarity	NPC103048
0.7447	Intermediate Similarity	NPC264022
0.7445	Intermediate Similarity	NPC55949
0.7444	Intermediate Similarity	NPC472681
0.7444	Intermediate Similarity	NPC275145
0.7444	Intermediate Similarity	NPC228739
0.7442	Intermediate Similarity	NPC471553
0.7442	Intermediate Similarity	NPC94425
0.744	Intermediate Similarity	NPC133308
0.744	Intermediate Similarity	NPC475002
0.744	Intermediate Similarity	NPC95126
0.744	Intermediate Similarity	NPC260818
0.7438	Intermediate Similarity	NPC255676
0.7436	Intermediate Similarity	NPC260233
0.7434	Intermediate Similarity	NPC67197
0.7432	Intermediate Similarity	NPC474310
0.7431	Intermediate Similarity	NPC474300
0.7429	Intermediate Similarity	NPC472372
0.7429	Intermediate Similarity	NPC472374
0.7426	Intermediate Similarity	NPC48248
0.7419	Intermediate Similarity	NPC470252
0.7419	Intermediate Similarity	NPC10251
0.7419	Intermediate Similarity	NPC17417
0.7417	Intermediate Similarity	NPC473325

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 NPC318067 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	809
0.2-0.3	1258
0.3-0.4	2638
0.4-0.5	2571
0.5-0.6	1287
0.6-0.7	331
0.7-0.8	44
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.819	Intermediate Similarity	NPD1931	Clinical (unspecified phase)
0.819	Intermediate Similarity	NPD1930	Approved
0.819	Intermediate Similarity	NPD1929	Approved
0.8103	Intermediate Similarity	NPD1932	Approved
0.8045	Intermediate Similarity	NPD7961	Discontinued
0.8017	Intermediate Similarity	NPD4141	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD2329	Discontinued
0.7931	Intermediate Similarity	NPD2066	Phase 3
0.7903	Intermediate Similarity	NPD5951	Approved
0.7812	Intermediate Similarity	NPD3412	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD5952	Clinical (unspecified phase)
0.7752	Intermediate Similarity	NPD4879	Approved
0.7674	Intermediate Similarity	NPD7163	Clinical (unspecified phase)
0.7672	Intermediate Similarity	NPD1989	Approved
0.763	Intermediate Similarity	NPD7008	Discontinued
0.7586	Intermediate Similarity	NPD688	Clinical (unspecified phase)
0.7561	Intermediate Similarity	NPD6831	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5122	Clinical (unspecified phase)
0.746	Intermediate Similarity	NPD7094	Approved
0.746	Intermediate Similarity	NPD6858	Approved
0.7458	Intermediate Similarity	NPD3495	Discontinued
0.7419	Intermediate Similarity	NPD2182	Approved
0.7414	Intermediate Similarity	NPD7631	Approved
0.7379	Intermediate Similarity	NPD7236	Approved
0.736	Intermediate Similarity	NPD1317	Discontinued
0.7348	Intermediate Similarity	NPD7457	Clinical (unspecified phase)
0.7328	Intermediate Similarity	NPD7609	Phase 3
0.7328	Intermediate Similarity	NPD1239	Approved
0.7311	Intermediate Similarity	NPD1565	Approved
0.7311	Intermediate Similarity	NPD1566	Phase 3
0.7311	Intermediate Similarity	NPD1564	Approved
0.7302	Intermediate Similarity	NPD2181	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD1693	Approved
0.7273	Intermediate Similarity	NPD2346	Discontinued
0.7248	Intermediate Similarity	NPD7239	Suspended
0.7244	Intermediate Similarity	NPD1609	Clinical (unspecified phase)
0.7241	Intermediate Similarity	NPD1089	Approved
0.7241	Intermediate Similarity	NPD1086	Approved
0.7241	Intermediate Similarity	NPD1090	Approved
0.7239	Intermediate Similarity	NPD4878	Approved
0.7236	Intermediate Similarity	NPD5909	Discontinued
0.7236	Intermediate Similarity	NPD1237	Approved
0.7209	Intermediate Similarity	NPD2629	Approved
0.7176	Intermediate Similarity	NPD7610	Discontinued
0.7155	Intermediate Similarity	NPD800	Approved
0.7154	Intermediate Similarity	NPD6647	Phase 2
0.7153	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2345	Approved
0.7123	Intermediate Similarity	NPD7003	Approved
0.7121	Intermediate Similarity	NPD7009	Phase 2
0.7119	Intermediate Similarity	NPD1088	Approved
0.7097	Intermediate Similarity	NPD164	Approved
0.7059	Intermediate Similarity	NPD1563	Approved
0.7049	Intermediate Similarity	NPD7798	Approved
0.7045	Intermediate Similarity	NPD6065	Approved
0.7037	Intermediate Similarity	NPD6287	Discontinued
0.7037	Intermediate Similarity	NPD5618	Discontinued
0.7034	Intermediate Similarity	NPD7702	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD2799	Discontinued
0.7007	Intermediate Similarity	NPD1283	Approved
0.7007	Intermediate Similarity	NPD8166	Discontinued
0.6983	Remote Similarity	NPD650	Approved
0.6983	Remote Similarity	NPD1087	Approved
0.6974	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD3226	Approved
0.6974	Remote Similarity	NPD7458	Discontinued
0.6966	Remote Similarity	NPD5408	Approved
0.6966	Remote Similarity	NPD5404	Approved
0.6966	Remote Similarity	NPD5406	Approved
0.6966	Remote Similarity	NPD5405	Approved
0.6957	Remote Similarity	NPD1470	Approved
0.6953	Remote Similarity	NPD2067	Discontinued
0.695	Remote Similarity	NPD2313	Discontinued
0.695	Remote Similarity	NPD3764	Approved
0.6911	Remote Similarity	NPD1238	Approved
0.6903	Remote Similarity	NPD7819	Suspended
0.6894	Remote Similarity	NPD4198	Discontinued
0.6863	Remote Similarity	NPD6591	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD2979	Phase 3
0.6853	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD5422	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD5981	Approved
0.6807	Remote Similarity	NPD3673	Approved
0.6807	Remote Similarity	NPD3672	Approved
0.6788	Remote Similarity	NPD4806	Approved
0.6788	Remote Similarity	NPD4807	Approved
0.6788	Remote Similarity	NPD1281	Approved
0.6786	Remote Similarity	NPD8150	Discontinued
0.6783	Remote Similarity	NPD6663	Approved
0.6781	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6779	Remote Similarity	NPD4628	Phase 3
0.6777	Remote Similarity	NPD1202	Approved
0.6776	Remote Similarity	NPD6273	Approved
0.6767	Remote Similarity	NPD3317	Approved
0.6765	Remote Similarity	NPD5306	Approved
0.6765	Remote Similarity	NPD5305	Approved
0.6755	Remote Similarity	NPD8165	Discontinued
0.6746	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD6010	Discontinued
0.6741	Remote Similarity	NPD4479	Discontinued
0.6738	Remote Similarity	NPD5736	Approved
0.6723	Remote Similarity	NPD5347	Phase 2
0.6723	Remote Similarity	NPD5346	Phase 2
0.6719	Remote Similarity	NPD6685	Approved
0.6715	Remote Similarity	NPD4136	Approved
0.6715	Remote Similarity	NPD4135	Approved
0.6715	Remote Similarity	NPD4106	Approved
0.6709	Remote Similarity	NPD7058	Phase 2
0.6709	Remote Similarity	NPD7057	Phase 3
0.6694	Remote Similarity	NPD1508	Approved
0.6691	Remote Similarity	NPD1245	Approved
0.6691	Remote Similarity	NPD182	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD7473	Discontinued
0.6667	Remote Similarity	NPD1201	Approved
0.6667	Remote Similarity	NPD7305	Phase 1
0.6667	Remote Similarity	NPD7714	Approved
0.6667	Remote Similarity	NPD2798	Approved
0.6667	Remote Similarity	NPD7715	Approved
0.6646	Remote Similarity	NPD7799	Discontinued
0.6643	Remote Similarity	NPD1876	Approved
0.6643	Remote Similarity	NPD6966	Discovery
0.6642	Remote Similarity	NPD2932	Approved
0.6641	Remote Similarity	NPD5048	Discontinued
0.6638	Remote Similarity	NPD9491	Approved
0.6626	Remote Similarity	NPD7997	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD2438	Suspended
0.6622	Remote Similarity	NPD2531	Phase 2
0.6619	Remote Similarity	NPD3972	Approved
0.6619	Remote Similarity	NPD6637	Approved
0.6617	Remote Similarity	NPD2652	Approved
0.6617	Remote Similarity	NPD2650	Approved
0.6601	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD3268	Approved
0.6596	Remote Similarity	NPD1164	Approved
0.6593	Remote Similarity	NPD4576	Approved
0.6593	Remote Similarity	NPD405	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD4574	Approved
0.6588	Remote Similarity	NPD8434	Phase 2
0.6585	Remote Similarity	NPD6049	Phase 2
0.6585	Remote Similarity	NPD6048	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1471	Phase 3
0.6575	Remote Similarity	NPD6355	Discontinued
0.6569	Remote Similarity	NPD1651	Approved
0.6569	Remote Similarity	NPD4105	Approved
0.6569	Remote Similarity	NPD4102	Approved
0.6567	Remote Similarity	NPD1246	Approved
0.6562	Remote Similarity	NPD7075	Discontinued
0.656	Remote Similarity	NPD9495	Approved
0.6556	Remote Similarity	NPD3750	Approved
0.6555	Remote Similarity	NPD4793	Discontinued
0.6554	Remote Similarity	NPD4308	Phase 3
0.6552	Remote Similarity	NPD7713	Phase 3
0.6549	Remote Similarity	NPD6085	Phase 2
0.6549	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD1843	Approved
0.6532	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6531	Remote Similarity	NPD3528	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD9256	Approved
0.6529	Remote Similarity	NPD9258	Approved
0.6522	Remote Similarity	NPD3019	Approved
0.6522	Remote Similarity	NPD4199	Phase 3
0.6512	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.651	Remote Similarity	NPD2935	Discontinued
0.6503	Remote Similarity	NPD7084	Phase 3
0.6503	Remote Similarity	NPD6232	Discontinued
0.65	Remote Similarity	NPD7768	Phase 2
0.6497	Remote Similarity	NPD6599	Discontinued
0.6496	Remote Similarity	NPD9545	Approved
0.6493	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD8368	Discontinued
0.6484	Remote Similarity	NPD5765	Approved
0.6479	Remote Similarity	NPD2797	Approved
0.6471	Remote Similarity	NPD3300	Phase 2
0.6466	Remote Similarity	NPD226	Approved
0.6466	Remote Similarity	NPD942	Approved
0.6458	Remote Similarity	NPD4620	Approved
0.6458	Remote Similarity	NPD5203	Approved
0.6458	Remote Similarity	NPD5201	Approved
0.6458	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD4617	Approved
0.6458	Remote Similarity	NPD6832	Phase 2
0.6454	Remote Similarity	NPD5159	Phase 2
0.6454	Remote Similarity	NPD5158	Clinical (unspecified phase)
0.6454	Remote Similarity	NPD5157	Phase 1
0.6449	Remote Similarity	NPD4196	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7177	Discontinued
0.6444	Remote Similarity	NPD4766	Approved
0.6443	Remote Similarity	NPD3748	Approved
0.6443	Remote Similarity	NPD3299	Clinical (unspecified phase)
0.6439	Remote Similarity	NPD3646	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD8032	Phase 2
0.6429	Remote Similarity	NPD7390	Discontinued
0.6418	Remote Similarity	NPD7635	Approved
0.6412	Remote Similarity	NPD8313	Approved
0.6412	Remote Similarity	NPD8312	Approved
0.6408	Remote Similarity	NPD1574	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