NPASS Compound

Structure

NPC217656 OpenBabel07101719252D 30 35 0 0 1 0 0 0 0 0999 V2000 -0.2863 -3.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6164 -0.8401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1187 1.6425 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1523 -1.8401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8843 0.1599 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0183 -0.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0183 -3.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7504 -0.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8843 -2.8401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1523 -0.1081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6523 -0.9741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4664 1.7405 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4177 2.2078 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7504 -2.3401 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2672 -0.5849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1730 2.3526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1523 -2.8401 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0183 -1.3401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5931 0.8420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5918 0.7897 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9993 0.0374 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7504 -1.3401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.6523 0.7580 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1523 -1.8401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8843 -1.8401 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7604 0.0242 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.4834 -0.5790 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.9501 1.7232 0.0000 N 0 0 0 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 1.3343 1.8079 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 22 1 0 0 0 0 5 6 1 0 0 0 0 5 8 1 0 0 0 0 6 18 1 0 0 0 0 7 9 1 0 0 0 0 7 17 1 0 0 0 0 8 22 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 30 1 0 0 0 0 14 22 1 0 0 0 0 14 25 1 0 0 0 0 15 26 2 0 0 0 0 15 27 1 0 0 0 0 16 28 2 0 0 0 0 16 30 1 0 0 0 0 17 24 1 1 0 0 0 18 24 1 6 0 0 0 18 25 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 19 30 1 0 0 0 0 20 26 1 0 0 0 0 20 28 1 0 0 0 0 21 27 2 0 0 0 0 21 29 1 0 0 0 0 22 25 1 1 0 0 0 23 3 1 6 0 0 0 23 29 1 0 0 0 0 24 4 1 6 0 0 0 25 9 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	407.3
Volume:	434.055
LogP:	4.761
LogD:	3.901
LogS:	-4.901
# Rotatable Bonds:	3
TPSA:	55.63
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	6
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.697
Synthetic Accessibility Score:	5.622
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.091
MDCK Permeability:	1.0253584150632378e-05
Pgp-inhibitor:	0.236
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.865
30% Bioavailability (F30%):	0.999

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.326
Plasma Protein Binding (PPB):	76.67439270019531%
Volume Distribution (VD):	1.891
Pgp-substrate:	18.257509231567383%

ADMET: Metabolism

CYP1A2-inhibitor:	0.039
CYP1A2-substrate:	0.884
CYP2C19-inhibitor:	0.077
CYP2C19-substrate:	0.251
CYP2C9-inhibitor:	0.119
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.181
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.917
CYP3A4-substrate:	0.697

ADMET: Excretion

Clearance (CL):	13.589
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.093
Human Hepatotoxicity (H-HT):	0.837
Drug-inuced Liver Injury (DILI):	0.706
AMES Toxicity:	0.448
Rat Oral Acute Toxicity:	0.148
Maximum Recommended Daily Dose:	0.923
Skin Sensitization:	0.943
Carcinogencity:	0.933
Eye Corrosion:	0.003
Eye Irritation:	0.011
Respiratory Toxicity:	0.787

Download Data

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

Natural Product: NPC217656

Natural Product ID:	NPC217656
*Common Name:**	Asmarine J
IUPAC Name:	n.a.
Synonyms:	Asmarine J
Standard InCHIKey:	OYPNTPXIXGAEFG-NDQMXJKWSA-N
Standard InCHI:	InChI=1S/C25H37N5/c1-17-7-9-25-14-22(25,2)8-5-6-18(25)24(17,4)11-10-23(3)12-13-30-16-28-20-19(30)21(29-23)27-15-26-20/h15-18H,5-14H2,1-4H3,(H,26,27,29)/t17-,18+,22-,23-,24-,25-/m0/s1
SMILES:	C[C@H]1CC[C@@]23[C@@H]([C@@]1(C)CC[C@@]1(C)CCn4c5c(N1)ncnc5nc4)CCC[C@]3(C2)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL491784
PubChem CID:	11395690
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001132] Pyrimidodiazepines

*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
NPO32472	raspailia sp.	Species	Raspailiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568794]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
GI50	13

Activity Type	# Activity
Cell Line	11
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT111	Cell Line	K562	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT81	Cell Line	A549	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT114	Cell Line	LoVo	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT858	Cell Line	LNCaP	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT134	Cell Line	SK-BR-3	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT461	Cell Line	PANC-1	Homo sapiens	GI50	=	5000.0	nM	PMID[448993]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	GI50	=	5000.0	nM	PMID[448993]

☑ 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 NPC217656 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	2400
0.1-0.2	25521
0.2-0.3	10618
0.3-0.4	3008
0.4-0.5	943
0.5-0.6	170
0.6-0.7	20
0.7-0.8	7
0.8-0.85	7
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9416	High Similarity	NPC244700
0.9338	High Similarity	NPC89139
0.8511	High Similarity	NPC476433
0.8511	High Similarity	NPC476528
0.8451	Intermediate Similarity	NPC476013
0.8451	Intermediate Similarity	NPC476522
0.8451	Intermediate Similarity	NPC474986
0.8392	Intermediate Similarity	NPC476521
0.8322	Intermediate Similarity	NPC476520
0.8298	Intermediate Similarity	NPC296437
0.8276	Intermediate Similarity	NPC476408
0.8239	Intermediate Similarity	NPC470266
0.7692	Intermediate Similarity	NPC472832
0.7692	Intermediate Similarity	NPC18308
0.7548	Intermediate Similarity	NPC472834
0.75	Intermediate Similarity	NPC472833
0.7099	Intermediate Similarity	NPC87981
0.7099	Intermediate Similarity	NPC174114
0.7018	Intermediate Similarity	NPC473585
0.6941	Remote Similarity	NPC164845
0.6857	Remote Similarity	NPC265111
0.6691	Remote Similarity	NPC18335
0.6667	Remote Similarity	NPC104011
0.6569	Remote Similarity	NPC476564
0.6494	Remote Similarity	NPC313897
0.6474	Remote Similarity	NPC33996
0.6471	Remote Similarity	NPC57279
0.6454	Remote Similarity	NPC4837
0.6454	Remote Similarity	NPC312187
0.6433	Remote Similarity	NPC129756
0.6414	Remote Similarity	NPC68938
0.6392	Remote Similarity	NPC317821
0.634	Remote Similarity	NPC246193
0.631	Remote Similarity	NPC93365
0.6289	Remote Similarity	NPC161659
0.6289	Remote Similarity	NPC209525
0.6213	Remote Similarity	NPC239737
0.6211	Remote Similarity	NPC229974
0.6211	Remote Similarity	NPC314152
0.6196	Remote Similarity	NPC189068
0.619	Remote Similarity	NPC189314
0.6176	Remote Similarity	NPC195140
0.6159	Remote Similarity	NPC309832
0.6159	Remote Similarity	NPC219313
0.6135	Remote Similarity	NPC107374
0.6135	Remote Similarity	NPC21448
0.6135	Remote Similarity	NPC156461
0.6124	Remote Similarity	NPC317054
0.6098	Remote Similarity	NPC164665
0.6084	Remote Similarity	NPC136349
0.6071	Remote Similarity	NPC328479
0.6061	Remote Similarity	NPC269827
0.6024	Remote Similarity	NPC121222
0.6012	Remote Similarity	NPC161224
0.6	Remote Similarity	NPC189261
0.5941	Remote Similarity	NPC212551
0.5941	Remote Similarity	NPC302778
0.5917	Remote Similarity	NPC211025
0.5917	Remote Similarity	NPC85689
0.5917	Remote Similarity	NPC185991
0.5909	Remote Similarity	NPC248007
0.5906	Remote Similarity	NPC174802
0.5899	Remote Similarity	NPC290959
0.589	Remote Similarity	NPC167285
0.5882	Remote Similarity	NPC472816
0.5882	Remote Similarity	NPC321814
0.5874	Remote Similarity	NPC476099
0.5872	Remote Similarity	NPC224076
0.5848	Remote Similarity	NPC164952
0.5848	Remote Similarity	NPC130586
0.5838	Remote Similarity	NPC226245
0.5806	Remote Similarity	NPC24589
0.5793	Remote Similarity	NPC76544
0.5793	Remote Similarity	NPC226184
0.5787	Remote Similarity	NPC325906
0.5765	Remote Similarity	NPC150853
0.5759	Remote Similarity	NPC14330
0.5747	Remote Similarity	NPC476297
0.5747	Remote Similarity	NPC316618
0.5734	Remote Similarity	NPC476561
0.573	Remote Similarity	NPC324484
0.5723	Remote Similarity	NPC287876
0.5722	Remote Similarity	NPC326082
0.5714	Remote Similarity	NPC313514
0.5714	Remote Similarity	NPC78941
0.5714	Remote Similarity	NPC139776
0.5714	Remote Similarity	NPC282458
0.5698	Remote Similarity	NPC207633
0.5674	Remote Similarity	NPC323091
0.5622	Remote Similarity	NPC477119
0.56	Remote Similarity	NPC52238

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 NPC217656 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	2024
0.2-0.3	3174
0.3-0.4	1995
0.4-0.5	1157
0.5-0.6	337
0.6-0.7	27
0.7-0.8	1
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
0.7817	Intermediate Similarity	NPD1058	Discontinued
0.7103	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.6691	Remote Similarity	NPD8836	Approved
0.6667	Remote Similarity	NPD248	Discontinued
0.6646	Remote Similarity	NPD7158	Phase 1
0.651	Remote Similarity	NPD9408	Phase 3
0.6506	Remote Similarity	NPD2646	Discontinued
0.6491	Remote Similarity	NPD2647	Phase 3
0.649	Remote Similarity	NPD9633	Phase 3
0.6478	Remote Similarity	NPD4240	Approved
0.6474	Remote Similarity	NPD799	Phase 1
0.6442	Remote Similarity	NPD3708	Phase 2
0.6433	Remote Similarity	NPD1313	Approved
0.642	Remote Similarity	NPD4183	Phase 3
0.642	Remote Similarity	NPD4182	Phase 3
0.6354	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD5682	Phase 3
0.6325	Remote Similarity	NPD3107	Discontinued
0.631	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD3695	Approved
0.6289	Remote Similarity	NPD193	Suspended
0.6289	Remote Similarity	NPD3696	Approved
0.6243	Remote Similarity	NPD1333	Phase 3
0.6215	Remote Similarity	NPD5666	Phase 2
0.6213	Remote Similarity	NPD2624	Phase 2
0.6211	Remote Similarity	NPD185	Approved
0.619	Remote Similarity	NPD8831	Approved
0.619	Remote Similarity	NPD8833	Approved
0.6154	Remote Similarity	NPD2456	Phase 2
0.6154	Remote Similarity	NPD2457	Phase 2
0.6149	Remote Similarity	NPD7988	Suspended
0.614	Remote Similarity	NPD5321	Phase 3
0.6135	Remote Similarity	NPD249	Approved
0.6135	Remote Similarity	NPD250	Approved
0.6135	Remote Similarity	NPD166	Approved
0.6131	Remote Similarity	NPD1369	Phase 2
0.6131	Remote Similarity	NPD1750	Clinical (unspecified phase)
0.6127	Remote Similarity	NPD1016	Phase 2
0.6127	Remote Similarity	NPD1015	Phase 2
0.6111	Remote Similarity	NPD2930	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD3378	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD548	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD5962	Phase 2
0.6069	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD195	Approved
0.6061	Remote Similarity	NPD186	Discovery
0.6045	Remote Similarity	NPD2875	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1732	Phase 3
0.6022	Remote Similarity	NPD3341	Clinical (unspecified phase)
0.6011	Remote Similarity	NPD1567	Clinical (unspecified phase)
0.5988	Remote Similarity	NPD2927	Phase 3
0.5979	Remote Similarity	NPD3485	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD6074	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.5975	Remote Similarity	NPD4763	Clinical (unspecified phase)
0.5959	Remote Similarity	NPD6816	Phase 3
0.5957	Remote Similarity	NPD3419	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD6761	Discontinued
0.5956	Remote Similarity	NPD2526	Phase 2
0.5956	Remote Similarity	NPD4649	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD2523	Phase 2
0.5949	Remote Similarity	NPD545	Clinical (unspecified phase)
0.5944	Remote Similarity	NPD3799	Suspended
0.5917	Remote Similarity	NPD283	Approved
0.5916	Remote Similarity	NPD7023	Clinical (unspecified phase)
0.5912	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.5909	Remote Similarity	NPD9084	Phase 2
0.5906	Remote Similarity	NPD339	Approved
0.5897	Remote Similarity	NPD6129	Phase 2
0.5872	Remote Similarity	NPD169	Phase 2
0.5868	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.586	Remote Similarity	NPD1807	Clinical (unspecified phase)
0.5848	Remote Similarity	NPD242	Approved
0.5848	Remote Similarity	NPD338	Approved
0.5843	Remote Similarity	NPD171	Discontinued
0.5842	Remote Similarity	NPD7722	Suspended
0.5838	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.5829	Remote Similarity	NPD2793	Discontinued
0.5829	Remote Similarity	NPD516	Clinical (unspecified phase)
0.5818	Remote Similarity	NPD2179	Discontinued
0.5817	Remote Similarity	NPD6850	Phase 2
0.5817	Remote Similarity	NPD6849	Phase 2
0.5808	Remote Similarity	NPD1730	Discontinued
0.5806	Remote Similarity	NPD1390	Phase 1
0.5806	Remote Similarity	NPD1389	Clinical (unspecified phase)
0.5806	Remote Similarity	NPD1388	Phase 1
0.5803	Remote Similarity	NPD5462	Discontinued
0.5798	Remote Similarity	NPD6418	Phase 1
0.5795	Remote Similarity	NPD3083	Approved
0.5789	Remote Similarity	NPD580	Discontinued
0.5787	Remote Similarity	NPD1777	Approved
0.5787	Remote Similarity	NPD1776	Approved
0.5783	Remote Similarity	NPD3706	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD5300	Clinical (unspecified phase)
0.5771	Remote Similarity	NPD6192	Phase 3
0.5761	Remote Similarity	NPD40	Phase 2
0.5761	Remote Similarity	NPD5730	Phase 2
0.5754	Remote Similarity	NPD1215	Discontinued
0.5754	Remote Similarity	NPD2478	Clinical (unspecified phase)
0.5746	Remote Similarity	NPD6828	Phase 2
0.5746	Remote Similarity	NPD6827	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD6417	Clinical (unspecified phase)
0.5745	Remote Similarity	NPD2591	Phase 2
0.5737	Remote Similarity	NPD5145	Clinical (unspecified phase)
0.5733	Remote Similarity	NPD757	Phase 3
0.5732	Remote Similarity	NPD1775	Approved
0.5732	Remote Similarity	NPD1085	Approved
0.5723	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5723	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.5722	Remote Similarity	NPD2333	Discontinued
0.5714	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD4352	Phase 1
0.5714	Remote Similarity	NPD7138	Phase 2
0.5707	Remote Similarity	NPD3041	Approved
0.5707	Remote Similarity	NPD7111	Discontinued
0.5706	Remote Similarity	NPD4709	Approved
0.5706	Remote Similarity	NPD6112	Approved
0.57	Remote Similarity	NPD7445	Phase 1
0.5699	Remote Similarity	NPD5806	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD8121	Phase 3
0.5698	Remote Similarity	NPD5269	Clinical (unspecified phase)
0.5698	Remote Similarity	NPD8120	Approved
0.5692	Remote Similarity	NPD6468	Clinical (unspecified phase)
0.5692	Remote Similarity	NPD6469	Phase 3
0.5689	Remote Similarity	NPD9704	Approved
0.5685	Remote Similarity	NPD6151	Phase 2
0.5677	Remote Similarity	NPD3431	Approved
0.5677	Remote Similarity	NPD3430	Approved
0.5677	Remote Similarity	NPD4262	Discontinued
0.5677	Remote Similarity	NPD4615	Phase 2
0.5677	Remote Similarity	NPD6619	Phase 3
0.5672	Remote Similarity	NPD6521	Phase 3
0.5672	Remote Similarity	NPD6520	Phase 3
0.5672	Remote Similarity	NPD4612	Discontinued
0.5667	Remote Similarity	NPD6794	Approved
0.5665	Remote Similarity	NPD213	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD214	Approved
0.5663	Remote Similarity	NPD2253	Discontinued
0.5661	Remote Similarity	NPD4902	Discontinued
0.5657	Remote Similarity	NPD5969	Clinical (unspecified phase)
0.5652	Remote Similarity	NPD547	Clinical (unspecified phase)
0.565	Remote Similarity	NPD7323	Phase 2
0.5645	Remote Similarity	NPD5508	Phase 1
0.5638	Remote Similarity	NPD5463	Clinical (unspecified phase)
0.5628	Remote Similarity	NPD3081	Clinical (unspecified phase)
0.5621	Remote Similarity	NPD578	Discontinued
0.5615	Remote Similarity	NPD1637	Clinical (unspecified phase)
0.5613	Remote Similarity	NPD6352	Phase 2
0.5611	Remote Similarity	NPD2135	Approved
0.5611	Remote Similarity	NPD2134	Approved
0.5611	Remote Similarity	NPD2136	Approved
0.561	Remote Similarity	NPD2602	Clinical (unspecified phase)
0.5605	Remote Similarity	NPD579	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