NPASS Compound

Structure

NPC138940 OpenBabel07101719242D 24 28 0 0 1 0 0 0 0 0999 V2000 3.1631 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -2.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 -1.2313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1631 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 -0.7313 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 1.4757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -1.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 2.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 1.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2971 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8084 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 0.2687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 1.7687 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5651 -0.5243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 -0.0243 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6744 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0576 0.7687 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4065 0.7687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5405 2.2687 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6945 1.2029 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 8 1 0 0 0 0 2 5 2 0 0 0 0 2 9 1 0 0 0 0 3 6 2 0 0 0 0 3 7 1 0 0 0 0 4 12 1 0 0 0 0 5 12 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 16 2 0 0 0 0 9 17 2 0 0 0 0 10 11 1 0 0 0 0 10 15 1 0 0 0 0 11 20 1 0 0 0 0 12 18 2 0 0 0 0 13 19 2 0 0 0 0 13 20 1 0 0 0 0 14 19 1 0 0 0 0 14 21 1 0 0 0 0 15 19 1 0 0 0 0 15 22 1 1 0 0 0 16 18 1 0 0 0 0 16 23 1 0 0 0 0 17 18 1 0 0 0 0 17 24 1 0 0 0 0 20 23 1 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	270.16
Volume:	304.533
LogP:	5.934
LogD:	4.393
LogS:	-4.731
# Rotatable Bonds:	5
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.828
Synthetic Accessibility Score:	2.066
Fsp3:	0.333
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:	-4.792
MDCK Permeability:	1.567376239108853e-05
Pgp-inhibitor:	0.986
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.839
30% Bioavailability (F30%):	0.997

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.112
Plasma Protein Binding (PPB):	99.16414642333984%
Volume Distribution (VD):	0.946
Pgp-substrate:	0.9063563346862793%

ADMET: Metabolism

CYP1A2-inhibitor:	0.95
CYP1A2-substrate:	0.631
CYP2C19-inhibitor:	0.933
CYP2C19-substrate:	0.068
CYP2C9-inhibitor:	0.702
CYP2C9-substrate:	0.946
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.918
CYP3A4-inhibitor:	0.286
CYP3A4-substrate:	0.243

ADMET: Excretion

Clearance (CL):	9.16
Half-life (T1/2):	0.327

ADMET: Toxicity

hERG Blockers:	0.047
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.159
AMES Toxicity:	0.355
Rat Oral Acute Toxicity:	0.213
Maximum Recommended Daily Dose:	0.469
Skin Sensitization:	0.935
Carcinogencity:	0.055
Eye Corrosion:	0.097
Eye Irritation:	0.95
Respiratory Toxicity:	0.108

Download Data

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

Natural Product: NPC138940

Natural Product ID:	NPC138940
*Common Name:**	VPWWOWTXVIXWBW-HNNXBMFYSA-N
IUPAC Name:	n.a.
Synonyms:	CJ-12371
Standard InCHIKey:	VPWWOWTXVIXWBW-HNNXBMFYSA-N
Standard InCHI:	InChI=1S/C20H16O4/c21-14-7-3-6-13-19(14)15(22)10-11-20(13)23-16-8-1-4-12-5-2-9-17(24-20)18(12)16/h1-9,15,21-22H,10-11H2/t15-/m0/s1
SMILES:	c1cc2cccc3c2c(c1)OC1(CC[C@@H](c2c1cccc2O)O)O3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL455963
PubChem CID:	487653
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000048] Tetralins

*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
NPO32660	edenia sp.	Species	Pleosporaceae	Eukaryota	n.a.	Panamanian	n.a.	PMID[19007286]

☑ 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	6
Others	1

Activity Type	# Activity
Cell Line	3
Organism	3
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT189	Cell Line	Vero	Chlorocebus aethiops	IC50	=	150000.0	nM	PMID[536044]
NPT4651	Cell Line	Ramos	Homo sapiens	IC50	>	100000.0	nM	PMID[536045]
NPT2341	Cell Line	NCI-H1975	Homo sapiens	IC50	>	100000.0	nM	PMID[536045]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	8400.0	nM	PMID[536044]
NPT580	Organism	Trypanosoma cruzi	Trypanosoma cruzi	IC50	=	26500.0	nM	PMID[536044]
NPT27	Others	Unspecified		Ratio IC50	=	8.0	n.a.	PMID[536044]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	>	10000.0	nM	PMID[536044]

☑ 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 NPC138940 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	404
0.1-0.2	1715
0.2-0.3	4769
0.3-0.4	13064
0.4-0.5	5077
0.5-0.6	5173
0.6-0.7	9777
0.7-0.8	2556
0.8-0.85	142
0.85-0.9	12
0.9-0.95	6
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.938	High Similarity	NPC284232
0.9323	High Similarity	NPC472151
0.9124	High Similarity	NPC151704
0.9111	High Similarity	NPC193920
0.9058	High Similarity	NPC271076
0.903	High Similarity	NPC92932
0.8849	High Similarity	NPC472155
0.8786	High Similarity	NPC472154
0.8786	High Similarity	NPC173630
0.8786	High Similarity	NPC23807
0.8777	High Similarity	NPC197461
0.8723	High Similarity	NPC288531
0.8592	High Similarity	NPC97662
0.8582	High Similarity	NPC257404
0.8511	High Similarity	NPC133585
0.8493	Intermediate Similarity	NPC233467
0.8429	Intermediate Similarity	NPC213607
0.8429	Intermediate Similarity	NPC174787
0.8429	Intermediate Similarity	NPC182509
0.8406	Intermediate Similarity	NPC11727
0.8406	Intermediate Similarity	NPC15109
0.8403	Intermediate Similarity	NPC301949
0.8403	Intermediate Similarity	NPC11800
0.8403	Intermediate Similarity	NPC206579
0.8392	Intermediate Similarity	NPC306816
0.8369	Intermediate Similarity	NPC473499
0.8346	Intermediate Similarity	NPC133407
0.8346	Intermediate Similarity	NPC28476
0.8346	Intermediate Similarity	NPC301321
0.8333	Intermediate Similarity	NPC102280
0.8333	Intermediate Similarity	NPC248053
0.8333	Intermediate Similarity	NPC155564
0.8298	Intermediate Similarity	NPC472794
0.8298	Intermediate Similarity	NPC473049
0.8286	Intermediate Similarity	NPC134260
0.8268	Intermediate Similarity	NPC470837
0.8261	Intermediate Similarity	NPC211352
0.8248	Intermediate Similarity	NPC153019
0.8243	Intermediate Similarity	NPC226108
0.8243	Intermediate Similarity	NPC59692
0.8243	Intermediate Similarity	NPC272552
0.8243	Intermediate Similarity	NPC322899
0.8243	Intermediate Similarity	NPC134911
0.8243	Intermediate Similarity	NPC46283
0.8243	Intermediate Similarity	NPC44192
0.8243	Intermediate Similarity	NPC21902
0.8243	Intermediate Similarity	NPC469944
0.8239	Intermediate Similarity	NPC472791
0.8239	Intermediate Similarity	NPC472792
0.8235	Intermediate Similarity	NPC97326
0.8235	Intermediate Similarity	NPC218003
0.8224	Intermediate Similarity	NPC100936
0.8224	Intermediate Similarity	NPC1253
0.8214	Intermediate Similarity	NPC475628
0.8214	Intermediate Similarity	NPC141717
0.8207	Intermediate Similarity	NPC47152
0.8201	Intermediate Similarity	NPC476615
0.8201	Intermediate Similarity	NPC476617
0.8201	Intermediate Similarity	NPC476616
0.8201	Intermediate Similarity	NPC473107
0.8195	Intermediate Similarity	NPC261992
0.8188	Intermediate Similarity	NPC78809
0.8188	Intermediate Similarity	NPC20050
0.8188	Intermediate Similarity	NPC289624
0.8188	Intermediate Similarity	NPC27578
0.8188	Intermediate Similarity	NPC306267
0.817	Intermediate Similarity	NPC73148
0.8162	Intermediate Similarity	NPC40377
0.8154	Intermediate Similarity	NPC283616
0.8143	Intermediate Similarity	NPC258780
0.8143	Intermediate Similarity	NPC125579
0.8143	Intermediate Similarity	NPC79957
0.8134	Intermediate Similarity	NPC61685
0.8129	Intermediate Similarity	NPC177712
0.8129	Intermediate Similarity	NPC24913
0.8125	Intermediate Similarity	NPC173203
0.8125	Intermediate Similarity	NPC163508
0.8125	Intermediate Similarity	NPC472451
0.8121	Intermediate Similarity	NPC474442
0.812	Intermediate Similarity	NPC188997
0.8116	Intermediate Similarity	NPC282508
0.8116	Intermediate Similarity	NPC472590
0.8116	Intermediate Similarity	NPC121376
0.8112	Intermediate Similarity	NPC210192
0.8112	Intermediate Similarity	NPC178054
0.8112	Intermediate Similarity	NPC100482
0.8112	Intermediate Similarity	NPC277331
0.8102	Intermediate Similarity	NPC471518
0.8102	Intermediate Similarity	NPC471519
0.8102	Intermediate Similarity	NPC472797
0.8095	Intermediate Similarity	NPC175976
0.8085	Intermediate Similarity	NPC206525
0.8085	Intermediate Similarity	NPC170328
0.8085	Intermediate Similarity	NPC472648
0.8085	Intermediate Similarity	NPC234952
0.8085	Intermediate Similarity	NPC472647
0.8085	Intermediate Similarity	NPC191462
0.8085	Intermediate Similarity	NPC133463
0.8085	Intermediate Similarity	NPC471522
0.8085	Intermediate Similarity	NPC472649
0.8082	Intermediate Similarity	NPC215678
0.8082	Intermediate Similarity	NPC274454
0.8082	Intermediate Similarity	NPC190714
0.8082	Intermediate Similarity	NPC99515
0.8074	Intermediate Similarity	NPC113495
0.8071	Intermediate Similarity	NPC130496
0.8071	Intermediate Similarity	NPC188555
0.8071	Intermediate Similarity	NPC71372
0.8069	Intermediate Similarity	NPC168579
0.8069	Intermediate Similarity	NPC171932
0.8069	Intermediate Similarity	NPC28440
0.8069	Intermediate Similarity	NPC304894
0.8069	Intermediate Similarity	NPC469313
0.8069	Intermediate Similarity	NPC76176
0.8069	Intermediate Similarity	NPC138227
0.8069	Intermediate Similarity	NPC15659
0.8058	Intermediate Similarity	NPC85799
0.8058	Intermediate Similarity	NPC165686
0.8058	Intermediate Similarity	NPC303422
0.8058	Intermediate Similarity	NPC189482
0.8058	Intermediate Similarity	NPC26080
0.8056	Intermediate Similarity	NPC186033
0.8056	Intermediate Similarity	NPC472353
0.8054	Intermediate Similarity	NPC259707
0.8054	Intermediate Similarity	NPC471403
0.8052	Intermediate Similarity	NPC48880
0.8043	Intermediate Similarity	NPC254000
0.8041	Intermediate Similarity	NPC295573
0.8041	Intermediate Similarity	NPC318373
0.8041	Intermediate Similarity	NPC470208
0.8041	Intermediate Similarity	NPC321657
0.8039	Intermediate Similarity	NPC472156
0.8029	Intermediate Similarity	NPC274717
0.8029	Intermediate Similarity	NPC47288
0.8028	Intermediate Similarity	NPC470307
0.8028	Intermediate Similarity	NPC71465
0.8028	Intermediate Similarity	NPC470308
0.8028	Intermediate Similarity	NPC472646
0.8028	Intermediate Similarity	NPC262328
0.8028	Intermediate Similarity	NPC87777
0.8027	Intermediate Similarity	NPC18185
0.8027	Intermediate Similarity	NPC174251
0.8027	Intermediate Similarity	NPC236202
0.8027	Intermediate Similarity	NPC204770
0.8027	Intermediate Similarity	NPC170103
0.8027	Intermediate Similarity	NPC70409
0.8027	Intermediate Similarity	NPC15538
0.8027	Intermediate Similarity	NPC58190
0.8027	Intermediate Similarity	NPC262911
0.8027	Intermediate Similarity	NPC294558
0.8027	Intermediate Similarity	NPC153182
0.8027	Intermediate Similarity	NPC108811
0.8027	Intermediate Similarity	NPC82917
0.8027	Intermediate Similarity	NPC202742
0.8027	Intermediate Similarity	NPC473480
0.8027	Intermediate Similarity	NPC263940
0.8015	Intermediate Similarity	NPC50315
0.8015	Intermediate Similarity	NPC26879
0.8015	Intermediate Similarity	NPC283049
0.8015	Intermediate Similarity	NPC230479
0.8014	Intermediate Similarity	NPC149633
0.8014	Intermediate Similarity	NPC37410
0.8014	Intermediate Similarity	NPC138915
0.8014	Intermediate Similarity	NPC238243
0.8	Intermediate Similarity	NPC469610
0.8	Intermediate Similarity	NPC115022
0.8	Intermediate Similarity	NPC252169
0.8	Intermediate Similarity	NPC294166
0.8	Intermediate Similarity	NPC215037
0.8	Intermediate Similarity	NPC37793
0.8	Intermediate Similarity	NPC473044
0.8	Intermediate Similarity	NPC248557
0.7986	Intermediate Similarity	NPC475067
0.7986	Intermediate Similarity	NPC473309
0.7986	Intermediate Similarity	NPC8899
0.7986	Intermediate Similarity	NPC5155
0.7974	Intermediate Similarity	NPC73517
0.7974	Intermediate Similarity	NPC4809
0.7974	Intermediate Similarity	NPC147743
0.7973	Intermediate Similarity	NPC329836
0.7973	Intermediate Similarity	NPC20757
0.7973	Intermediate Similarity	NPC280945
0.7973	Intermediate Similarity	NPC227516
0.7972	Intermediate Similarity	NPC292487
0.7972	Intermediate Similarity	NPC471388
0.7972	Intermediate Similarity	NPC32630
0.7972	Intermediate Similarity	NPC183781
0.7971	Intermediate Similarity	NPC16577
0.7971	Intermediate Similarity	NPC96719
0.7971	Intermediate Similarity	NPC222108
0.797	Intermediate Similarity	NPC100108
0.797	Intermediate Similarity	NPC277798
0.7959	Intermediate Similarity	NPC473951
0.7959	Intermediate Similarity	NPC71686
0.7959	Intermediate Similarity	NPC125755
0.7959	Intermediate Similarity	NPC96576
0.7959	Intermediate Similarity	NPC176804
0.7958	Intermediate Similarity	NPC138350
0.7958	Intermediate Similarity	NPC40664
0.7958	Intermediate Similarity	NPC3293

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 NPC138940 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	357
0.1-0.2	948
0.2-0.3	1677
0.3-0.4	2716
0.4-0.5	1695
0.5-0.6	1096
0.6-0.7	588
0.7-0.8	71
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
0.8162	Intermediate Similarity	NPD4908	Phase 1
0.8043	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7971	Intermediate Similarity	NPD4625	Phase 3
0.7956	Intermediate Similarity	NPD2861	Phase 2
0.791	Intermediate Similarity	NPD1091	Approved
0.7885	Intermediate Similarity	NPD3787	Discontinued
0.7801	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7801	Intermediate Similarity	NPD1613	Approved
0.7786	Intermediate Similarity	NPD6671	Approved
0.7778	Intermediate Similarity	NPD1610	Phase 2
0.7748	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7638	Intermediate Similarity	NPD968	Approved
0.7619	Intermediate Similarity	NPD6674	Discontinued
0.7612	Intermediate Similarity	NPD1548	Phase 1
0.7578	Intermediate Similarity	NPD3751	Discontinued
0.7552	Intermediate Similarity	NPD4060	Phase 1
0.7548	Intermediate Similarity	NPD8455	Phase 2
0.7536	Intermediate Similarity	NPD4749	Approved
0.7535	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7519	Intermediate Similarity	NPD709	Approved
0.7518	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD3496	Discontinued
0.741	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7097	Phase 1
0.7391	Intermediate Similarity	NPD1611	Approved
0.7376	Intermediate Similarity	NPD6584	Phase 3
0.7375	Intermediate Similarity	NPD6959	Discontinued
0.7347	Intermediate Similarity	NPD4108	Discontinued
0.7343	Intermediate Similarity	NPD3027	Phase 3
0.7338	Intermediate Similarity	NPD2235	Phase 2
0.7338	Intermediate Similarity	NPD1653	Approved
0.7338	Intermediate Similarity	NPD2231	Phase 2
0.7317	Intermediate Similarity	NPD5844	Phase 1
0.7315	Intermediate Similarity	NPD7037	Approved
0.731	Intermediate Similarity	NPD4140	Approved
0.7308	Intermediate Similarity	NPD290	Approved
0.7305	Intermediate Similarity	NPD8312	Approved
0.7305	Intermediate Similarity	NPD8313	Approved
0.7303	Intermediate Similarity	NPD7041	Phase 2
0.7303	Intermediate Similarity	NPD7213	Phase 3
0.7303	Intermediate Similarity	NPD7212	Phase 2
0.7303	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD7447	Phase 1
0.7241	Intermediate Similarity	NPD6233	Phase 2
0.7239	Intermediate Similarity	NPD1398	Phase 1
0.7219	Intermediate Similarity	NPD3892	Phase 2
0.7206	Intermediate Similarity	NPD7340	Approved
0.7188	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7183	Intermediate Similarity	NPD2797	Approved
0.7176	Intermediate Similarity	NPD2342	Discontinued
0.7172	Intermediate Similarity	NPD6798	Discontinued
0.7172	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD6582	Phase 2
0.7163	Intermediate Similarity	NPD5327	Phase 3
0.7163	Intermediate Similarity	NPD6583	Phase 3
0.716	Intermediate Similarity	NPD7199	Phase 2
0.7152	Intermediate Similarity	NPD7228	Approved
0.7152	Intermediate Similarity	NPD37	Approved
0.7143	Intermediate Similarity	NPD5735	Approved
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD5763	Approved
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4965	Approved
0.7125	Intermediate Similarity	NPD4966	Approved
0.7123	Intermediate Similarity	NPD4474	Approved
0.7123	Intermediate Similarity	NPD4475	Approved
0.7122	Intermediate Similarity	NPD5846	Approved
0.7122	Intermediate Similarity	NPD6516	Phase 2
0.7114	Intermediate Similarity	NPD2154	Approved
0.7114	Intermediate Similarity	NPD2155	Approved
0.7114	Intermediate Similarity	NPD2156	Approved
0.7113	Intermediate Similarity	NPD3225	Approved
0.7113	Intermediate Similarity	NPD6696	Suspended
0.7108	Intermediate Similarity	NPD7054	Approved
0.7105	Intermediate Similarity	NPD3750	Approved
0.7078	Intermediate Similarity	NPD6087	Phase 1
0.7067	Intermediate Similarity	NPD6100	Approved
0.7067	Intermediate Similarity	NPD6099	Approved
0.7066	Intermediate Similarity	NPD7472	Approved
0.7066	Intermediate Similarity	NPD7074	Phase 3
0.7055	Intermediate Similarity	NPD3268	Approved
0.7055	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD3443	Approved
0.705	Intermediate Similarity	NPD3444	Approved
0.705	Intermediate Similarity	NPD3445	Approved
0.705	Intermediate Similarity	NPD5585	Approved
0.7047	Intermediate Similarity	NPD7119	Phase 2
0.7037	Intermediate Similarity	NPD5535	Approved
0.7037	Intermediate Similarity	NPD7635	Approved
0.7037	Intermediate Similarity	NPD6234	Discontinued
0.703	Intermediate Similarity	NPD6166	Phase 2
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD5124	Phase 1
0.7027	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6797	Phase 2
0.7021	Intermediate Similarity	NPD3705	Approved
0.702	Intermediate Similarity	NPD7266	Discontinued
0.7019	Intermediate Similarity	NPD7768	Phase 2
0.7013	Intermediate Similarity	NPD5058	Phase 3
0.7007	Intermediate Similarity	NPD7157	Approved
0.7	Intermediate Similarity	NPD5126	Approved
0.7	Intermediate Similarity	NPD7033	Discontinued
0.7	Intermediate Similarity	NPD4626	Approved
0.7	Intermediate Similarity	NPD5125	Phase 3
0.6993	Remote Similarity	NPD7003	Approved
0.6992	Remote Similarity	NPD2684	Approved
0.6987	Remote Similarity	NPD6273	Approved
0.6986	Remote Similarity	NPD7095	Approved
0.6985	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD7251	Discontinued
0.6982	Remote Similarity	NPD6559	Discontinued
0.698	Remote Similarity	NPD4097	Suspended
0.698	Remote Similarity	NPD6353	Approved
0.698	Remote Similarity	NPD6653	Approved
0.6972	Remote Similarity	NPD2233	Approved
0.6972	Remote Similarity	NPD1840	Phase 2
0.6972	Remote Similarity	NPD2232	Approved
0.6972	Remote Similarity	NPD2230	Approved
0.697	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD5837	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD2238	Phase 2
0.6959	Remote Similarity	NPD3620	Phase 2
0.6959	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD5402	Approved
0.6954	Remote Similarity	NPD6032	Approved
0.6954	Remote Similarity	NPD2935	Discontinued
0.6948	Remote Similarity	NPD2677	Approved
0.6941	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4536	Approved
0.6933	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4538	Approved
0.6929	Remote Similarity	NPD5691	Approved
0.6929	Remote Similarity	NPD1357	Approved
0.6928	Remote Similarity	NPD5177	Phase 3
0.6928	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3685	Discontinued
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6918	Remote Similarity	NPD600	Approved
0.6918	Remote Similarity	NPD596	Approved
0.6914	Remote Similarity	NPD7879	Clinical (unspecified phase)
0.6913	Remote Similarity	NPD6355	Discontinued
0.6912	Remote Similarity	NPD7843	Approved
0.6909	Remote Similarity	NPD7229	Phase 3
0.6908	Remote Similarity	NPD2346	Discontinued
0.6908	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1535	Discovery
0.6901	Remote Similarity	NPD422	Phase 1
0.6897	Remote Similarity	NPD558	Phase 2
0.6894	Remote Similarity	NPD7819	Suspended
0.6894	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD5929	Approved
0.6892	Remote Similarity	NPD839	Approved
0.6892	Remote Similarity	NPD7477	Discontinued
0.6892	Remote Similarity	NPD840	Approved
0.6887	Remote Similarity	NPD5588	Approved
0.6887	Remote Similarity	NPD5960	Phase 3
0.6883	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD6090	Discontinued
0.6879	Remote Similarity	NPD1778	Approved
0.6871	Remote Similarity	NPD3749	Approved
0.6863	Remote Similarity	NPD1549	Phase 2
0.6861	Remote Similarity	NPD5283	Phase 1
0.6857	Remote Similarity	NPD3091	Approved
0.6853	Remote Similarity	NPD1481	Phase 2
0.6849	Remote Similarity	NPD1712	Approved
0.6845	Remote Similarity	NPD3818	Discontinued
0.6835	Remote Similarity	NPD7427	Discontinued
0.6832	Remote Similarity	NPD1934	Approved
0.6828	Remote Similarity	NPD3094	Phase 2
0.6828	Remote Similarity	NPD1203	Approved
0.6818	Remote Similarity	NPD5061	Approved
0.6818	Remote Similarity	NPD5062	Approved
0.6818	Remote Similarity	NPD1652	Phase 2
0.6815	Remote Similarity	NPD5451	Approved
0.6815	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4380	Phase 2
0.6809	Remote Similarity	NPD6382	Discontinued
0.6806	Remote Similarity	NPD4359	Approved
0.68	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD7030	Discontinued
0.6797	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7240	Approved
0.6781	Remote Similarity	NPD4624	Approved
0.6776	Remote Similarity	NPD3748	Approved
0.6774	Remote Similarity	NPD7466	Approved
0.677	Remote Similarity	NPD7411	Suspended
0.6763	Remote Similarity	NPD6387	Discontinued
0.6763	Remote Similarity	NPD2557	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