NPASS Compound

Structure

CID186284 OpenBabel06191715562D 25 30 0 0 1 0 0 0 0 0999 V2000 -2.8628 -1.6526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8626 -0.5503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9090 -2.2036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9085 0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7202 0.8280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9548 1.1968 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5615 -0.7069 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0487 -2.6184 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9318 -3.0191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4651 -1.4275 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8627 -1.6537 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4222 -1.9762 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4856 -1.1292 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9091 -0.0004 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8630 -0.5514 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9543 -1.6529 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9541 -0.5507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9087 -2.2044 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.1892 0.8283 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9544 -0.5510 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9542 -1.6533 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7203 -2.4547 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.2928 -2.5703 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7142 1.5491 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 3 1 0 0 0 0 2 4 1 0 0 0 0 3 16 2 0 0 0 0 4 17 2 0 0 0 0 5 6 1 0 0 0 0 5 14 2 0 0 0 0 6 19 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 9 1 0 0 0 0 9 22 1 0 0 0 0 10 24 1 0 0 0 0 11 18 1 0 0 0 0 12 13 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 11 1 1 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 23 1 0 0 0 0 18 21 1 6 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 19 25 2 0 0 0 0 20 21 1 1 0 0 0 20 23 1 0 0 0 0 21 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	334.17
Volume:	344.189
LogP:	1.214
LogD:	1.472
LogS:	-3.256
# Rotatable Bonds:	1
TPSA:	43.78
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.797
Synthetic Accessibility Score:	5.783
Fsp3:	0.476
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.727
MDCK Permeability:	2.0234312614775263e-05
Pgp-inhibitor:	0.313
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.927
20% Bioavailability (F20%):	0.954
30% Bioavailability (F30%):	0.808

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.977
Plasma Protein Binding (PPB):	49.7222900390625%
Volume Distribution (VD):	1.102
Pgp-substrate:	56.63123321533203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.055
CYP1A2-substrate:	0.157
CYP2C19-inhibitor:	0.036
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.374
CYP2D6-inhibitor:	0.112
CYP2D6-substrate:	0.36
CYP3A4-inhibitor:	0.313
CYP3A4-substrate:	0.899

ADMET: Excretion

Clearance (CL):	4.813
Half-life (T1/2):	0.571

ADMET: Toxicity

hERG Blockers:	0.075
Human Hepatotoxicity (H-HT):	0.544
Drug-inuced Liver Injury (DILI):	0.623
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.928
Maximum Recommended Daily Dose:	0.975
Skin Sensitization:	0.85
Carcinogencity:	0.751
Eye Corrosion:	0.004
Eye Irritation:	0.033
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC186284

Natural Product ID:	NPC186284
*Common Name:**	Isostrychnine
IUPAC Name:	n.a.
Synonyms:	Isostrychnine
Standard InCHIKey:	PNYOGGAOQVIZDM-JQNVFVSUSA-N
Standard InCHI:	InChI=1S/C21H22N2O2/c24-10-7-13-12-22-9-8-21-16-3-1-2-4-17(16)23-19(25)6-5-14(20(21)23)15(13)11-18(21)22/h1-5,7,15,18,20,24H,6,8-12H2/b13-7-/t15-,18-,20-,21+/m0/s1
SMILES:	c1ccc2c(c1)[C@]13CCN4C/C(=C/CO)/[C@H](C[C@@H]14)C1=CCC(=O)N2[C@H]31
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2164628
PubChem CID:	11024113
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002749] Strychnos 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
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	DOI[10.1016/j.tet.2012.03.006]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[16317898]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[17449162]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[19235686]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19666019]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[22707864]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23088673]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[2393954]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[25594733]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	seed	n.a.	PMID[7912074]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28245	Strychnos nux-vomica	Species	Loganiaceae	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	5

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT660	Cell Line	SW480	Homo sapiens	IC50	>	40000.0	nM	PMID[512748]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	40000.0	nM	PMID[512748]
NPT81	Cell Line	A549	Homo sapiens	IC50	>	40000.0	nM	PMID[512748]
NPT659	Cell Line	SMMC-7721	Homo sapiens	IC50	>	40000.0	nM	PMID[512748]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	>	40000.0	nM	PMID[512748]

☑ 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 NPC186284 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	207
0.1-0.2	1370
0.2-0.3	7239
0.3-0.4	23043
0.4-0.5	7802
0.5-0.6	2581
0.6-0.7	380
0.7-0.8	72
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC22082
0.8435	Intermediate Similarity	NPC154602
0.838	Intermediate Similarity	NPC130251
0.8188	Intermediate Similarity	NPC243756
0.8187	Intermediate Similarity	NPC286994
0.8133	Intermediate Similarity	NPC285381
0.8117	Intermediate Similarity	NPC472117
0.8069	Intermediate Similarity	NPC301760
0.7959	Intermediate Similarity	NPC469537
0.7895	Intermediate Similarity	NPC122106
0.78	Intermediate Similarity	NPC264589
0.7764	Intermediate Similarity	NPC251212
0.7764	Intermediate Similarity	NPC214626
0.7764	Intermediate Similarity	NPC139085
0.7742	Intermediate Similarity	NPC469536
0.7712	Intermediate Similarity	NPC66936
0.7688	Intermediate Similarity	NPC475248
0.7688	Intermediate Similarity	NPC63047
0.7673	Intermediate Similarity	NPC472106
0.7671	Intermediate Similarity	NPC471123
0.7658	Intermediate Similarity	NPC472120
0.7658	Intermediate Similarity	NPC472101
0.7654	Intermediate Similarity	NPC473743
0.7632	Intermediate Similarity	NPC212799
0.7595	Intermediate Similarity	NPC225319
0.7595	Intermediate Similarity	NPC472102
0.7595	Intermediate Similarity	NPC309531
0.7484	Intermediate Similarity	NPC475763
0.7468	Intermediate Similarity	NPC104345
0.7468	Intermediate Similarity	NPC109787
0.7468	Intermediate Similarity	NPC113946
0.7421	Intermediate Similarity	NPC36495
0.741	Intermediate Similarity	NPC260075
0.7384	Intermediate Similarity	NPC22689
0.7384	Intermediate Similarity	NPC105055
0.7361	Intermediate Similarity	NPC478079
0.7358	Intermediate Similarity	NPC222029
0.7333	Intermediate Similarity	NPC469560
0.7329	Intermediate Similarity	NPC282339
0.7329	Intermediate Similarity	NPC469741
0.7329	Intermediate Similarity	NPC99632
0.7312	Intermediate Similarity	NPC471122
0.7303	Intermediate Similarity	NPC127178
0.7301	Intermediate Similarity	NPC279527
0.7301	Intermediate Similarity	NPC214960
0.7289	Intermediate Similarity	NPC475097
0.7256	Intermediate Similarity	NPC33507
0.7239	Intermediate Similarity	NPC471124
0.7238	Intermediate Similarity	NPC329833
0.7226	Intermediate Similarity	NPC469735
0.7214	Intermediate Similarity	NPC264580
0.7205	Intermediate Similarity	NPC193410
0.7197	Intermediate Similarity	NPC318086
0.7179	Intermediate Similarity	NPC469740
0.7171	Intermediate Similarity	NPC243162
0.716	Intermediate Similarity	NPC68650
0.716	Intermediate Similarity	NPC248117
0.7143	Intermediate Similarity	NPC123241
0.7143	Intermediate Similarity	NPC61013
0.7135	Intermediate Similarity	NPC162440
0.7126	Intermediate Similarity	NPC473880
0.7126	Intermediate Similarity	NPC96901
0.7099	Intermediate Similarity	NPC276085
0.7086	Intermediate Similarity	NPC267508
0.7063	Intermediate Similarity	NPC475915
0.7062	Intermediate Similarity	NPC470485
0.7059	Intermediate Similarity	NPC315051
0.7059	Intermediate Similarity	NPC99043
0.7059	Intermediate Similarity	NPC218594
0.7052	Intermediate Similarity	NPC52262
0.7045	Intermediate Similarity	NPC470483
0.7013	Intermediate Similarity	NPC470301
0.7012	Intermediate Similarity	NPC293458
0.6981	Remote Similarity	NPC473329
0.6975	Remote Similarity	NPC29285
0.6946	Remote Similarity	NPC223595
0.6946	Remote Similarity	NPC224970
0.6946	Remote Similarity	NPC167724
0.6941	Remote Similarity	NPC320147
0.6928	Remote Similarity	NPC475420
0.6917	Remote Similarity	NPC291610
0.6892	Remote Similarity	NPC476950
0.6882	Remote Similarity	NPC470548
0.6879	Remote Similarity	NPC311330
0.6852	Remote Similarity	NPC478076
0.6848	Remote Similarity	NPC474058
0.6848	Remote Similarity	NPC201424
0.6848	Remote Similarity	NPC315368
0.6842	Remote Similarity	NPC203202
0.6842	Remote Similarity	NPC264482
0.6833	Remote Similarity	NPC221687
0.6832	Remote Similarity	NPC206592
0.6831	Remote Similarity	NPC67904
0.6831	Remote Similarity	NPC138830
0.6824	Remote Similarity	NPC285622
0.6824	Remote Similarity	NPC242269
0.6807	Remote Similarity	NPC286871
0.6805	Remote Similarity	NPC469915
0.6805	Remote Similarity	NPC472118
0.68	Remote Similarity	NPC2933
0.68	Remote Similarity	NPC97584
0.6796	Remote Similarity	NPC97100
0.6796	Remote Similarity	NPC473375
0.6765	Remote Similarity	NPC355
0.6763	Remote Similarity	NPC6974
0.6761	Remote Similarity	NPC307396
0.6761	Remote Similarity	NPC259626
0.6759	Remote Similarity	NPC316582
0.6758	Remote Similarity	NPC472542
0.6758	Remote Similarity	NPC472541
0.6743	Remote Similarity	NPC256288
0.6736	Remote Similarity	NPC228515
0.6732	Remote Similarity	NPC313352
0.6724	Remote Similarity	NPC11149
0.6711	Remote Similarity	NPC53044
0.6707	Remote Similarity	NPC85651
0.6707	Remote Similarity	NPC176983
0.6705	Remote Similarity	NPC14325
0.6705	Remote Similarity	NPC28848
0.6705	Remote Similarity	NPC470003
0.6705	Remote Similarity	NPC186669
0.6704	Remote Similarity	NPC128582
0.6703	Remote Similarity	NPC472540
0.6703	Remote Similarity	NPC470787
0.6703	Remote Similarity	NPC472539
0.6688	Remote Similarity	NPC471164
0.6687	Remote Similarity	NPC472100
0.6686	Remote Similarity	NPC472114
0.6686	Remote Similarity	NPC472115
0.6667	Remote Similarity	NPC145754
0.6647	Remote Similarity	NPC476441
0.663	Remote Similarity	NPC471386
0.6629	Remote Similarity	NPC473615
0.6627	Remote Similarity	NPC211525
0.6627	Remote Similarity	NPC153694
0.6613	Remote Similarity	NPC471512
0.6607	Remote Similarity	NPC476231
0.6606	Remote Similarity	NPC470507
0.66	Remote Similarity	NPC250476
0.6592	Remote Similarity	NPC229484
0.659	Remote Similarity	NPC469726
0.659	Remote Similarity	NPC329338
0.6579	Remote Similarity	NPC226662
0.6562	Remote Similarity	NPC472103
0.6556	Remote Similarity	NPC292675
0.6554	Remote Similarity	NPC159963
0.6552	Remote Similarity	NPC192209
0.6548	Remote Similarity	NPC143457
0.6541	Remote Similarity	NPC100863
0.6536	Remote Similarity	NPC231382
0.6534	Remote Similarity	NPC24864
0.6519	Remote Similarity	NPC5630
0.6516	Remote Similarity	NPC162417
0.6516	Remote Similarity	NPC316104
0.651	Remote Similarity	NPC283130
0.651	Remote Similarity	NPC328683
0.6509	Remote Similarity	NPC194881
0.6508	Remote Similarity	NPC470484
0.6507	Remote Similarity	NPC220698
0.6503	Remote Similarity	NPC187036
0.6494	Remote Similarity	NPC473962
0.649	Remote Similarity	NPC252794
0.6488	Remote Similarity	NPC148468
0.6488	Remote Similarity	NPC63210
0.6488	Remote Similarity	NPC263709
0.6488	Remote Similarity	NPC310403
0.6488	Remote Similarity	NPC97380
0.6488	Remote Similarity	NPC243673
0.6486	Remote Similarity	NPC257490
0.6485	Remote Similarity	NPC117032
0.6484	Remote Similarity	NPC276430
0.6484	Remote Similarity	NPC129909
0.6484	Remote Similarity	NPC203628
0.6483	Remote Similarity	NPC313673
0.6481	Remote Similarity	NPC324445
0.648	Remote Similarity	NPC476095
0.6477	Remote Similarity	NPC475094
0.6471	Remote Similarity	NPC313757
0.6471	Remote Similarity	NPC328270
0.6471	Remote Similarity	NPC475489
0.6467	Remote Similarity	NPC477156
0.6467	Remote Similarity	NPC477157
0.6463	Remote Similarity	NPC291962
0.6463	Remote Similarity	NPC177684
0.6463	Remote Similarity	NPC37548
0.6461	Remote Similarity	NPC477159
0.6457	Remote Similarity	NPC129624
0.6446	Remote Similarity	NPC295021
0.6442	Remote Similarity	NPC254798
0.6438	Remote Similarity	NPC313449
0.6437	Remote Similarity	NPC161861
0.6437	Remote Similarity	NPC476425
0.6429	Remote Similarity	NPC473298
0.6429	Remote Similarity	NPC473569
0.6429	Remote Similarity	NPC299594
0.6425	Remote Similarity	NPC475422
0.6424	Remote Similarity	NPC470343
0.6424	Remote Similarity	NPC79698
0.6424	Remote Similarity	NPC472244
0.642	Remote Similarity	NPC116519

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 NPC186284 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	155
0.1-0.2	558
0.2-0.3	775
0.3-0.4	1672
0.4-0.5	3595
0.5-0.6	2074
0.6-0.7	303
0.7-0.8	16
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8133	Intermediate Similarity	NPD8402	Approved
0.8133	Intermediate Similarity	NPD8401	Approved
0.8133	Intermediate Similarity	NPD8400	Approved
0.7744	Intermediate Similarity	NPD5179	Approved
0.7744	Intermediate Similarity	NPD5180	Approved
0.7744	Intermediate Similarity	NPD5181	Approved
0.7698	Intermediate Similarity	NPD3623	Clinical (unspecified phase)
0.7698	Intermediate Similarity	NPD3622	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6396	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6395	Phase 2
0.7386	Intermediate Similarity	NPD6017	Discontinued
0.7376	Intermediate Similarity	NPD4775	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD4430	Phase 2
0.7351	Intermediate Similarity	NPD2093	Discontinued
0.7347	Intermediate Similarity	NPD6740	Clinical (unspecified phase)
0.7343	Intermediate Similarity	NPD5136	Clinical (unspecified phase)
0.7313	Intermediate Similarity	NPD4116	Approved
0.7266	Intermediate Similarity	NPD2638	Clinical (unspecified phase)
0.7248	Intermediate Similarity	NPD2791	Discontinued
0.7214	Intermediate Similarity	NPD5657	Phase 3
0.7211	Intermediate Similarity	NPD6489	Phase 3
0.7174	Intermediate Similarity	NPD5631	Phase 3
0.7163	Intermediate Similarity	NPD1306	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8630	Approved
0.7143	Intermediate Similarity	NPD5527	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5526	Phase 2
0.7086	Intermediate Similarity	NPD6102	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD7633	Discontinued
0.7055	Intermediate Similarity	NPD2840	Approved
0.7037	Intermediate Similarity	NPD5715	Clinical (unspecified phase)
0.702	Intermediate Similarity	NPD6318	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD5993	Phase 1
0.6985	Remote Similarity	NPD1721	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1668	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD6566	Discontinued
0.6963	Remote Similarity	NPD1064	Approved
0.6963	Remote Similarity	NPD1065	Approved
0.6962	Remote Similarity	NPD7441	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD4121	Phase 3
0.6957	Remote Similarity	NPD4120	Approved
0.6943	Remote Similarity	NPD5933	Phase 3
0.6943	Remote Similarity	NPD5932	Phase 3
0.6943	Remote Similarity	NPD5931	Phase 3
0.6928	Remote Similarity	NPD6358	Phase 2
0.6928	Remote Similarity	NPD4411	Phase 1
0.6928	Remote Similarity	NPD4410	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD4939	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD5743	Approved
0.6914	Remote Similarity	NPD5741	Approved
0.6914	Remote Similarity	NPD5742	Approved
0.6913	Remote Similarity	NPD5131	Approved
0.6857	Remote Similarity	NPD2913	Approved
0.6857	Remote Similarity	NPD2914	Approved
0.6855	Remote Similarity	NPD7794	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2038	Approved
0.6835	Remote Similarity	NPD2039	Approved
0.6831	Remote Similarity	NPD6070	Approved
0.6831	Remote Similarity	NPD6069	Approved
0.6831	Remote Similarity	NPD1344	Phase 2
0.6829	Remote Similarity	NPD8060	Phase 1
0.6824	Remote Similarity	NPD3240	Phase 2
0.6821	Remote Similarity	NPD6879	Phase 2
0.6821	Remote Similarity	NPD6878	Phase 2
0.6815	Remote Similarity	NPD4464	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4942	Approved
0.6813	Remote Similarity	NPD5881	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD5629	Discontinued
0.68	Remote Similarity	NPD4365	Phase 2
0.6792	Remote Similarity	NPD3141	Discontinued
0.6788	Remote Similarity	NPD4114	Approved
0.6788	Remote Similarity	NPD7599	Phase 2
0.6788	Remote Similarity	NPD4115	Approved
0.6757	Remote Similarity	NPD6792	Phase 3
0.6735	Remote Similarity	NPD519	Approved
0.6731	Remote Similarity	NPD6606	Clinical (unspecified phase)
0.673	Remote Similarity	NPD5060	Phase 1
0.6728	Remote Similarity	NPD3277	Phase 3
0.6728	Remote Similarity	NPD6575	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD7735	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD3546	Approved
0.6715	Remote Similarity	NPD3545	Approved
0.6714	Remote Similarity	NPD3865	Approved
0.671	Remote Similarity	NPD3864	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD2820	Phase 3
0.6688	Remote Similarity	NPD3625	Discontinued
0.6667	Remote Similarity	NPD6655	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1663	Discontinued
0.6667	Remote Similarity	NPD5918	Discontinued
0.6667	Remote Similarity	NPD5253	Approved
0.6667	Remote Similarity	NPD6855	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6557	Phase 2
0.6647	Remote Similarity	NPD7600	Phase 2
0.6646	Remote Similarity	NPD2365	Approved
0.6646	Remote Similarity	NPD2426	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD6768	Approved
0.6646	Remote Similarity	NPD2790	Discontinued
0.6645	Remote Similarity	NPD3118	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD3080	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD7295	Approved
0.6625	Remote Similarity	NPD6622	Phase 1
0.6623	Remote Similarity	NPD7200	Approved
0.6623	Remote Similarity	NPD4549	Discontinued
0.6621	Remote Similarity	NPD6343	Approved
0.6621	Remote Similarity	NPD6345	Approved
0.662	Remote Similarity	NPD3387	Approved
0.6607	Remote Similarity	NPD5551	Clinical (unspecified phase)
0.6603	Remote Similarity	NPD6342	Discontinued
0.66	Remote Similarity	NPD6900	Discontinued
0.6584	Remote Similarity	NPD3278	Clinical (unspecified phase)
0.6582	Remote Similarity	NPD6789	Approved
0.6582	Remote Similarity	NPD3434	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD3551	Approved
0.6562	Remote Similarity	NPD7487	Discontinued
0.6562	Remote Similarity	NPD4347	Clinical (unspecified phase)
0.6561	Remote Similarity	NPD7254	Discontinued
0.6552	Remote Similarity	NPD5990	Approved
0.6552	Remote Similarity	NPD5991	Approved
0.6548	Remote Similarity	NPD6454	Clinical (unspecified phase)
0.6544	Remote Similarity	NPD708	Approved
0.6544	Remote Similarity	NPD4735	Approved
0.6544	Remote Similarity	NPD4734	Approved
0.6536	Remote Similarity	NPD4300	Clinical (unspecified phase)
0.6519	Remote Similarity	NPD5068	Clinical (unspecified phase)
0.651	Remote Similarity	NPD478	Approved
0.6506	Remote Similarity	NPD7072	Phase 2
0.6506	Remote Similarity	NPD5606	Discontinued
0.6503	Remote Similarity	NPD5942	Approved
0.6503	Remote Similarity	NPD5941	Approved
0.6503	Remote Similarity	NPD979	Approved
0.65	Remote Similarity	NPD5024	Approved
0.65	Remote Similarity	NPD5020	Approved
0.6485	Remote Similarity	NPD3248	Phase 1
0.6484	Remote Similarity	NPD8240	Discontinued
0.6484	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6483	Remote Similarity	NPD7679	Phase 2
0.6481	Remote Similarity	NPD5839	Clinical (unspecified phase)
0.6479	Remote Similarity	NPD2999	Approved
0.6479	Remote Similarity	NPD3001	Approved
0.6471	Remote Similarity	NPD4019	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD3790	Phase 2
0.6464	Remote Similarity	NPD4334	Discontinued
0.646	Remote Similarity	NPD6506	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD5104	Approved
0.6454	Remote Similarity	NPD4063	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD1527	Phase 2
0.6452	Remote Similarity	NPD2950	Approved
0.6452	Remote Similarity	NPD2949	Approved
0.6446	Remote Similarity	NPD7612	Clinical (unspecified phase)
0.6446	Remote Similarity	NPD7774	Clinical (unspecified phase)
0.6443	Remote Similarity	NPD4178	Approved
0.6443	Remote Similarity	NPD4176	Approved
0.6442	Remote Similarity	NPD1886	Approved
0.6438	Remote Similarity	NPD7480	Approved
0.6438	Remote Similarity	NPD7481	Approved
0.6433	Remote Similarity	NPD7591	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4783	Approved
0.6429	Remote Similarity	NPD4781	Approved
0.6425	Remote Similarity	NPD5923	Phase 1
0.6424	Remote Similarity	NPD5578	Approved
0.6424	Remote Similarity	NPD8128	Discontinued
0.6424	Remote Similarity	NPD5577	Clinical (unspecified phase)
0.6424	Remote Similarity	NPD6320	Approved
0.642	Remote Similarity	NPD5600	Discontinued
0.6417	Remote Similarity	NPD6248	Phase 2
0.6417	Remote Similarity	NPD6249	Phase 2
0.6414	Remote Similarity	NPD2622	Approved
0.6414	Remote Similarity	NPD1723	Phase 2
0.6414	Remote Similarity	NPD1720	Phase 2
0.641	Remote Similarity	NPD5184	Approved
0.641	Remote Similarity	NPD5185	Approved
0.641	Remote Similarity	NPD3034	Discontinued
0.641	Remote Similarity	NPD5182	Approved
0.6405	Remote Similarity	NPD995	Clinical (unspecified phase)
0.6402	Remote Similarity	NPD4682	Phase 2
0.6402	Remote Similarity	NPD5423	Phase 2
0.64	Remote Similarity	NPD7461	Approved
0.6398	Remote Similarity	NPD2129	Approved
0.6398	Remote Similarity	NPD6206	Phase 1
0.6398	Remote Similarity	NPD6301	Phase 2
0.6398	Remote Similarity	NPD7082	Approved
0.6395	Remote Similarity	NPD5823	Approved
0.6392	Remote Similarity	NPD5318	Discontinued
0.6391	Remote Similarity	NPD4393	Approved
0.6391	Remote Similarity	NPD33	Approved
0.6389	Remote Similarity	NPD1175	Approved
0.6386	Remote Similarity	NPD6707	Clinical (unspecified phase)
0.6382	Remote Similarity	NPD2113	Approved
0.638	Remote Similarity	NPD1524	Phase 1
0.6379	Remote Similarity	NPD3824	Phase 1
0.6375	Remote Similarity	NPD1953	Discontinued
0.6375	Remote Similarity	NPD5518	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD2010	Phase 3
0.637	Remote Similarity	NPD6660	Discontinued
0.6364	Remote Similarity	NPD2918	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD2919	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6261	Phase 3
0.6364	Remote Similarity	NPD4075	Phase 2
0.6358	Remote Similarity	NPD7259	Approved
0.6358	Remote Similarity	NPD2938	Approved
0.6358	Remote Similarity	NPD2940	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