NPASS Compound

Structure

NPC105803 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 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 0.8660 -1.5000 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 -1.7321 -0.0000 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 0.8660 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 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 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 -2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 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 -3.2321 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 5 6 1 0 0 0 0 5 12 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 17 1 0 0 0 0 8 19 1 0 0 0 0 9 13 2 0 0 0 0 9 14 1 0 0 0 0 10 12 1 0 0 0 0 10 17 1 0 0 0 0 11 15 1 0 0 0 0 11 18 1 0 0 0 0 12 19 1 1 0 0 0 13 15 1 0 0 0 0 13 20 1 0 0 0 0 14 18 1 1 0 0 0 14 19 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 0 0 0 0 16 22 2 0 0 0 0 16 23 1 0 0 0 0 17 2 1 6 0 0 0 18 3 1 6 0 0 0 19 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.18
Volume:	336.126
LogP:	2.818
LogD:	1.515
LogS:	-3.974
# Rotatable Bonds:	1
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.752
Synthetic Accessibility Score:	4.614
Fsp3:	0.737
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.396
MDCK Permeability:	2.4956074412330054e-05
Pgp-inhibitor:	0.516
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	90.9276123046875%
Volume Distribution (VD):	0.4
Pgp-substrate:	8.549271583557129%

ADMET: Metabolism

CYP1A2-inhibitor:	0.01
CYP1A2-substrate:	0.936
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.055
CYP2C9-substrate:	0.192
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.056
CYP3A4-inhibitor:	0.335
CYP3A4-substrate:	0.34

ADMET: Excretion

Clearance (CL):	0.983
Half-life (T1/2):	0.471

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.545
Drug-inuced Liver Injury (DILI):	0.088
AMES Toxicity:	0.46
Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.73
Skin Sensitization:	0.65
Carcinogencity:	0.818
Eye Corrosion:	0.344
Eye Irritation:	0.132
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC105803

Natural Product ID:	NPC105803
*Common Name:**	Ent-16-Nor-5Alpha,13Alpha(Methyl)-3-Oxodolabra-1,4(18)-Dien-2-Ol-15-Oic Acid
IUPAC Name:	(2S,4aS,4bR,8aS,10aS)-6-hydroxy-2,4a,8a-trimethyl-8-methylidene-7-oxo-3,4,4b,9,10,10a-hexahydro-1H-phenanthrene-2-carboxylic acid
Synonyms:
Standard InCHIKey:	CVAILKMOFONEDU-KRJMWWHISA-N
Standard InCHI:	InChI=1S/C19H26O4/c1-11-15(21)13(20)9-14-18(11,3)6-5-12-10-17(2,16(22)23)7-8-19(12,14)4/h9,12,14,20H,1,5-8,10H2,2-4H3,(H,22,23)/t12-,14-,17-,18+,19-/m0/s1
SMILES:	O=C1C(=C[C@H]2[C@](C1=C)(C)CC[C@@H]1[C@]2(C)CC[C@](C1)(C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL499143
PubChem CID:	15765122
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001194] Oxosteroids

*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
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	stem bark	Philippines	n.a.	PMID[16562829]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24597894]
NPO9878	Dichapetalum gelonioides	Species	Dichapetalaceae	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
ED50	9

Activity Type	# Activity
Cell Line	8
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1034	Cell Line	Lu1	Homo sapiens	ED50	=	3.8	ug ml-1	PMID[570767]
NPT1851	Cell Line	Col2	Homo sapiens	ED50	=	2.7	ug ml-1	PMID[570767]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[570767]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	4.3	ug ml-1	PMID[570767]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[570767]
NPT858	Cell Line	LNCaP	Homo sapiens	ED50	=	3.7	ug ml-1	PMID[570767]
NPT2345	Cell Line	SW626	Homo sapiens	ED50	=	5.0	ug ml-1	PMID[570767]
NPT136	Cell Line	SK-N-SH	Homo sapiens	ED50	=	9.0	ug ml-1	PMID[570767]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	ED50	=	4.0	ug ml-1	PMID[570767]

☑ 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 NPC105803 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	178
0.1-0.2	1174
0.2-0.3	5251
0.3-0.4	13864
0.4-0.5	9788
0.5-0.6	6726
0.6-0.7	4137
0.7-0.8	1418
0.8-0.85	123
0.85-0.9	31
0.9-0.95	5
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9747	High Similarity	NPC474680
0.9481	High Similarity	NPC192329
0.9241	High Similarity	NPC55869
0.9241	High Similarity	NPC278459
0.9114	High Similarity	NPC108955
0.9048	High Similarity	NPC112454
0.9024	High Similarity	NPC241512
0.9024	High Similarity	NPC6185
0.8974	High Similarity	NPC165711
0.8861	High Similarity	NPC74410
0.8861	High Similarity	NPC30321
0.8846	High Similarity	NPC92080
0.8846	High Similarity	NPC180886
0.8837	High Similarity	NPC174167
0.8837	High Similarity	NPC470036
0.8795	High Similarity	NPC263997
0.8795	High Similarity	NPC8518
0.8795	High Similarity	NPC132228
0.8765	High Similarity	NPC471898
0.875	High Similarity	NPC147232
0.8736	High Similarity	NPC263780
0.8675	High Similarity	NPC96095
0.8659	High Similarity	NPC302661
0.8659	High Similarity	NPC103486
0.8659	High Similarity	NPC238991
0.8625	High Similarity	NPC476808
0.8608	High Similarity	NPC69143
0.8605	High Similarity	NPC477973
0.8571	High Similarity	NPC29447
0.8571	High Similarity	NPC474537
0.8554	High Similarity	NPC102197
0.8554	High Similarity	NPC53733
0.8554	High Similarity	NPC49019
0.8539	High Similarity	NPC777
0.8537	High Similarity	NPC90055
0.8537	High Similarity	NPC225515
0.8519	High Similarity	NPC199595
0.8519	High Similarity	NPC27817
0.8506	High Similarity	NPC475823
0.8506	High Similarity	NPC474209
0.85	High Similarity	NPC472300
0.85	High Similarity	NPC97377
0.8488	Intermediate Similarity	NPC48107
0.8481	Intermediate Similarity	NPC279666
0.8481	Intermediate Similarity	NPC192540
0.8434	Intermediate Similarity	NPC251779
0.8434	Intermediate Similarity	NPC69101
0.8434	Intermediate Similarity	NPC320514
0.8415	Intermediate Similarity	NPC476809
0.8415	Intermediate Similarity	NPC26139
0.8415	Intermediate Similarity	NPC37038
0.8415	Intermediate Similarity	NPC2482
0.8415	Intermediate Similarity	NPC18955
0.8395	Intermediate Similarity	NPC280654
0.8395	Intermediate Similarity	NPC189485
0.8395	Intermediate Similarity	NPC476810
0.8395	Intermediate Similarity	NPC110094
0.8395	Intermediate Similarity	NPC260385
0.8395	Intermediate Similarity	NPC198240
0.8391	Intermediate Similarity	NPC65615
0.8391	Intermediate Similarity	NPC262043
0.8391	Intermediate Similarity	NPC68148
0.8375	Intermediate Similarity	NPC1254
0.8372	Intermediate Similarity	NPC476409
0.8372	Intermediate Similarity	NPC136948
0.8354	Intermediate Similarity	NPC241854
0.8354	Intermediate Similarity	NPC103958
0.8354	Intermediate Similarity	NPC283908
0.8354	Intermediate Similarity	NPC476046
0.8354	Intermediate Similarity	NPC183503
0.8354	Intermediate Similarity	NPC161923
0.8354	Intermediate Similarity	NPC251970
0.8353	Intermediate Similarity	NPC469993
0.8333	Intermediate Similarity	NPC168188
0.8333	Intermediate Similarity	NPC470015
0.8313	Intermediate Similarity	NPC274050
0.8313	Intermediate Similarity	NPC162632
0.8313	Intermediate Similarity	NPC147066
0.8313	Intermediate Similarity	NPC267691
0.8313	Intermediate Similarity	NPC474085
0.8313	Intermediate Similarity	NPC121984
0.8313	Intermediate Similarity	NPC263272
0.8313	Intermediate Similarity	NPC477372
0.8295	Intermediate Similarity	NPC252737
0.8293	Intermediate Similarity	NPC231431
0.8276	Intermediate Similarity	NPC72397
0.8272	Intermediate Similarity	NPC471899
0.8272	Intermediate Similarity	NPC107039
0.8272	Intermediate Similarity	NPC471897
0.8272	Intermediate Similarity	NPC476811
0.8272	Intermediate Similarity	NPC61952
0.8256	Intermediate Similarity	NPC94666
0.8256	Intermediate Similarity	NPC229717
0.825	Intermediate Similarity	NPC476795
0.825	Intermediate Similarity	NPC175079
0.8235	Intermediate Similarity	NPC248758
0.8235	Intermediate Similarity	NPC237712
0.8235	Intermediate Similarity	NPC144258
0.8222	Intermediate Similarity	NPC23170
0.8214	Intermediate Similarity	NPC260956
0.8202	Intermediate Similarity	NPC230064
0.8193	Intermediate Similarity	NPC469637
0.8193	Intermediate Similarity	NPC477057
0.8193	Intermediate Similarity	NPC104545
0.8171	Intermediate Similarity	NPC321514
0.8171	Intermediate Similarity	NPC59436
0.8148	Intermediate Similarity	NPC89294
0.8148	Intermediate Similarity	NPC110725
0.8148	Intermediate Similarity	NPC309399
0.814	Intermediate Similarity	NPC123319
0.814	Intermediate Similarity	NPC133652
0.814	Intermediate Similarity	NPC94531
0.814	Intermediate Similarity	NPC33663
0.814	Intermediate Similarity	NPC311702
0.8132	Intermediate Similarity	NPC295347
0.8118	Intermediate Similarity	NPC258985
0.8118	Intermediate Similarity	NPC70834
0.8118	Intermediate Similarity	NPC97913
0.8111	Intermediate Similarity	NPC211230
0.8111	Intermediate Similarity	NPC271652
0.8105	Intermediate Similarity	NPC179208
0.8101	Intermediate Similarity	NPC160817
0.8095	Intermediate Similarity	NPC472684
0.8095	Intermediate Similarity	NPC44963
0.8095	Intermediate Similarity	NPC475863
0.8095	Intermediate Similarity	NPC142244
0.8095	Intermediate Similarity	NPC473217
0.8095	Intermediate Similarity	NPC470034
0.8095	Intermediate Similarity	NPC99308
0.8095	Intermediate Similarity	NPC201912
0.8095	Intermediate Similarity	NPC116797
0.8095	Intermediate Similarity	NPC38350
0.8095	Intermediate Similarity	NPC475833
0.8095	Intermediate Similarity	NPC221647
0.809	Intermediate Similarity	NPC476437
0.809	Intermediate Similarity	NPC46441
0.809	Intermediate Similarity	NPC476369
0.8072	Intermediate Similarity	NPC477371
0.8072	Intermediate Similarity	NPC16394
0.8068	Intermediate Similarity	NPC474474
0.8068	Intermediate Similarity	NPC1753
0.8068	Intermediate Similarity	NPC473229
0.8068	Intermediate Similarity	NPC474511
0.8049	Intermediate Similarity	NPC212661
0.8049	Intermediate Similarity	NPC471035
0.8046	Intermediate Similarity	NPC327115
0.8046	Intermediate Similarity	NPC472869
0.8025	Intermediate Similarity	NPC201027
0.8023	Intermediate Similarity	NPC164577
0.8023	Intermediate Similarity	NPC156981
0.8023	Intermediate Similarity	NPC19849
0.8023	Intermediate Similarity	NPC472865
0.8023	Intermediate Similarity	NPC472864
0.8022	Intermediate Similarity	NPC474882
0.8022	Intermediate Similarity	NPC474328
0.8	Intermediate Similarity	NPC4036
0.8	Intermediate Similarity	NPC26865
0.8	Intermediate Similarity	NPC472813
0.8	Intermediate Similarity	NPC158030
0.8	Intermediate Similarity	NPC233455
0.8	Intermediate Similarity	NPC193347
0.8	Intermediate Similarity	NPC35656
0.8	Intermediate Similarity	NPC133391
0.8	Intermediate Similarity	NPC204341
0.8	Intermediate Similarity	NPC73882
0.8	Intermediate Similarity	NPC65120
0.8	Intermediate Similarity	NPC100297
0.8	Intermediate Similarity	NPC145067
0.8	Intermediate Similarity	NPC474525
0.7978	Intermediate Similarity	NPC310010
0.7978	Intermediate Similarity	NPC5509
0.7978	Intermediate Similarity	NPC474918
0.7978	Intermediate Similarity	NPC474700
0.7978	Intermediate Similarity	NPC326627
0.7978	Intermediate Similarity	NPC118011
0.7978	Intermediate Similarity	NPC305039
0.7978	Intermediate Similarity	NPC36668
0.7976	Intermediate Similarity	NPC472478
0.7976	Intermediate Similarity	NPC287063
0.7976	Intermediate Similarity	NPC474956
0.7957	Intermediate Similarity	NPC170131
0.7957	Intermediate Similarity	NPC208094
0.7957	Intermediate Similarity	NPC108078
0.7955	Intermediate Similarity	NPC477228
0.7955	Intermediate Similarity	NPC220930
0.7955	Intermediate Similarity	NPC158141
0.7955	Intermediate Similarity	NPC96496
0.7955	Intermediate Similarity	NPC272039
0.7955	Intermediate Similarity	NPC173089
0.7952	Intermediate Similarity	NPC179028
0.7952	Intermediate Similarity	NPC471409
0.7952	Intermediate Similarity	NPC275494
0.7931	Intermediate Similarity	NPC473038
0.7931	Intermediate Similarity	NPC142649
0.7931	Intermediate Similarity	NPC32037
0.7931	Intermediate Similarity	NPC255174
0.7931	Intermediate Similarity	NPC90287
0.7931	Intermediate Similarity	NPC469948
0.7927	Intermediate Similarity	NPC470525
0.7917	Intermediate Similarity	NPC230918

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 NPC105803 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1606
0.2-0.3	3834
0.3-0.4	2328
0.4-0.5	745
0.5-0.6	203
0.6-0.7	134
0.7-0.8	114
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9359	High Similarity	NPD4695	Discontinued
0.9048	High Similarity	NPD7285	Clinical (unspecified phase)
0.8625	High Similarity	NPD3617	Approved
0.8235	Intermediate Similarity	NPD4197	Approved
0.814	Intermediate Similarity	NPD5329	Approved
0.8068	Intermediate Similarity	NPD6672	Approved
0.8068	Intermediate Similarity	NPD5737	Approved
0.8046	Intermediate Similarity	NPD5690	Phase 2
0.8046	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.8	Intermediate Similarity	NPD7515	Phase 2
0.7978	Intermediate Similarity	NPD6904	Approved
0.7978	Intermediate Similarity	NPD6673	Approved
0.7978	Intermediate Similarity	NPD6080	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7957	Intermediate Similarity	NPD6084	Phase 2
0.7957	Intermediate Similarity	NPD6083	Phase 2
0.7935	Intermediate Similarity	NPD5695	Phase 3
0.7872	Intermediate Similarity	NPD5696	Approved
0.7849	Intermediate Similarity	NPD7614	Phase 1
0.7841	Intermediate Similarity	NPD5280	Approved
0.7841	Intermediate Similarity	NPD4694	Approved
0.7826	Intermediate Similarity	NPD7748	Approved
0.7816	Intermediate Similarity	NPD3665	Phase 1
0.7816	Intermediate Similarity	NPD3666	Approved
0.7816	Intermediate Similarity	NPD3133	Approved
0.7802	Intermediate Similarity	NPD5693	Phase 1
0.7802	Intermediate Similarity	NPD5281	Approved
0.7802	Intermediate Similarity	NPD5284	Approved
0.7791	Intermediate Similarity	NPD3667	Approved
0.7753	Intermediate Similarity	NPD3573	Approved
0.7742	Intermediate Similarity	NPD4629	Approved
0.7742	Intermediate Similarity	NPD5210	Approved
0.7717	Intermediate Similarity	NPD6399	Phase 3
0.7692	Intermediate Similarity	NPD5692	Phase 3
0.766	Intermediate Similarity	NPD5221	Approved
0.766	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD5222	Approved
0.764	Intermediate Similarity	NPD4689	Approved
0.764	Intermediate Similarity	NPD4693	Phase 3
0.764	Intermediate Similarity	NPD4623	Approved
0.764	Intermediate Similarity	NPD4690	Approved
0.764	Intermediate Similarity	NPD6409	Approved
0.764	Intermediate Similarity	NPD5205	Approved
0.764	Intermediate Similarity	NPD4688	Approved
0.764	Intermediate Similarity	NPD4138	Approved
0.764	Intermediate Similarity	NPD5330	Approved
0.764	Intermediate Similarity	NPD7334	Approved
0.764	Intermediate Similarity	NPD4519	Discontinued
0.764	Intermediate Similarity	NPD7146	Approved
0.764	Intermediate Similarity	NPD6098	Approved
0.764	Intermediate Similarity	NPD5279	Phase 3
0.764	Intermediate Similarity	NPD6684	Approved
0.764	Intermediate Similarity	NPD7521	Approved
0.764	Intermediate Similarity	NPD3618	Phase 1
0.7614	Intermediate Similarity	NPD4786	Approved
0.7609	Intermediate Similarity	NPD6050	Approved
0.7609	Intermediate Similarity	NPD5694	Approved
0.7579	Intermediate Similarity	NPD7902	Approved
0.7579	Intermediate Similarity	NPD5173	Approved
0.7532	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD4691	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7474	Intermediate Similarity	NPD4697	Phase 3
0.7473	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5208	Approved
0.7473	Intermediate Similarity	NPD6903	Approved
0.7442	Intermediate Similarity	NPD4195	Approved
0.7426	Intermediate Similarity	NPD6899	Approved
0.7426	Intermediate Similarity	NPD6881	Approved
0.7426	Intermediate Similarity	NPD6011	Approved
0.7423	Intermediate Similarity	NPD4696	Approved
0.7423	Intermediate Similarity	NPD5285	Approved
0.7423	Intermediate Similarity	NPD5286	Approved
0.7419	Intermediate Similarity	NPD6079	Approved
0.7416	Intermediate Similarity	NPD3668	Phase 3
0.7407	Intermediate Similarity	NPD4137	Phase 3
0.74	Intermediate Similarity	NPD7128	Approved
0.74	Intermediate Similarity	NPD5739	Approved
0.74	Intermediate Similarity	NPD6675	Approved
0.74	Intermediate Similarity	NPD6402	Approved
0.7396	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD5328	Approved
0.7386	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5654	Approved
0.7353	Intermediate Similarity	NPD6012	Approved
0.7353	Intermediate Similarity	NPD6014	Approved
0.7353	Intermediate Similarity	NPD6013	Approved
0.7347	Intermediate Similarity	NPD5223	Approved
0.734	Intermediate Similarity	NPD5133	Approved
0.7327	Intermediate Similarity	NPD5701	Approved
0.7317	Intermediate Similarity	NPD4747	Approved
0.7292	Intermediate Similarity	NPD7732	Phase 3
0.7282	Intermediate Similarity	NPD7102	Approved
0.7282	Intermediate Similarity	NPD6883	Approved
0.7282	Intermediate Similarity	NPD7290	Approved
0.7273	Intermediate Similarity	NPD4633	Approved
0.7273	Intermediate Similarity	NPD5225	Approved
0.7273	Intermediate Similarity	NPD5091	Approved
0.7273	Intermediate Similarity	NPD5226	Approved
0.7273	Intermediate Similarity	NPD5224	Approved
0.7273	Intermediate Similarity	NPD5211	Phase 2
0.7263	Intermediate Similarity	NPD7900	Approved
0.7263	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD4058	Approved
0.7255	Intermediate Similarity	NPD7320	Approved
0.7245	Intermediate Similarity	NPD4700	Approved
0.7216	Intermediate Similarity	NPD5959	Approved
0.7212	Intermediate Similarity	NPD8130	Phase 1
0.7212	Intermediate Similarity	NPD6617	Approved
0.7212	Intermediate Similarity	NPD6869	Approved
0.7212	Intermediate Similarity	NPD6650	Approved
0.7212	Intermediate Similarity	NPD6847	Approved
0.7212	Intermediate Similarity	NPD6649	Approved
0.72	Intermediate Similarity	NPD5175	Approved
0.72	Intermediate Similarity	NPD5174	Approved
0.7188	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD6372	Approved
0.7184	Intermediate Similarity	NPD6373	Approved
0.7158	Intermediate Similarity	NPD4202	Approved
0.7143	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD8297	Approved
0.7129	Intermediate Similarity	NPD5141	Approved
0.7128	Intermediate Similarity	NPD5207	Approved
0.7111	Intermediate Similarity	NPD4788	Approved
0.7083	Intermediate Similarity	NPD6001	Approved
0.7079	Intermediate Similarity	NPD4139	Approved
0.7079	Intermediate Similarity	NPD4692	Approved
0.7075	Intermediate Similarity	NPD4632	Approved
0.7048	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD4224	Phase 2
0.703	Intermediate Similarity	NPD4754	Approved
0.7011	Intermediate Similarity	NPD4756	Discovery
0.699	Remote Similarity	NPD6614	Approved
0.6957	Remote Similarity	NPD1694	Approved
0.6947	Remote Similarity	NPD4096	Approved
0.6944	Remote Similarity	NPD6274	Approved
0.6944	Remote Similarity	NPD6868	Approved
0.6923	Remote Similarity	NPD4729	Approved
0.6923	Remote Similarity	NPD4730	Approved
0.6923	Remote Similarity	NPD5128	Approved
0.6923	Remote Similarity	NPD5168	Approved
0.6915	Remote Similarity	NPD4518	Approved
0.6914	Remote Similarity	NPD7341	Phase 2
0.69	Remote Similarity	NPD6404	Discontinued
0.6893	Remote Similarity	NPD4768	Approved
0.6893	Remote Similarity	NPD4767	Approved
0.6881	Remote Similarity	NPD6317	Approved
0.6881	Remote Similarity	NPD6009	Approved
0.6875	Remote Similarity	NPD6411	Approved
0.6867	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4687	Approved
0.686	Remote Similarity	NPD5733	Approved
0.6829	Remote Similarity	NPD7331	Phase 2
0.6824	Remote Similarity	NPD6081	Approved
0.6824	Remote Similarity	NPD5276	Approved
0.6818	Remote Similarity	NPD6335	Approved
0.6818	Remote Similarity	NPD6313	Approved
0.6818	Remote Similarity	NPD6314	Approved
0.68	Remote Similarity	NPD7638	Approved
0.6792	Remote Similarity	NPD5250	Approved
0.6792	Remote Similarity	NPD5135	Approved
0.6792	Remote Similarity	NPD5251	Approved
0.6792	Remote Similarity	NPD5169	Approved
0.6792	Remote Similarity	NPD5248	Approved
0.6792	Remote Similarity	NPD4634	Approved
0.6792	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD5247	Approved
0.6792	Remote Similarity	NPD5249	Phase 3
0.6778	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD1696	Phase 3
0.6757	Remote Similarity	NPD7100	Approved
0.6757	Remote Similarity	NPD7101	Approved
0.6733	Remote Similarity	NPD7639	Approved
0.6733	Remote Similarity	NPD7640	Approved
0.6731	Remote Similarity	NPD6008	Approved
0.6729	Remote Similarity	NPD5215	Approved
0.6729	Remote Similarity	NPD5127	Approved
0.6729	Remote Similarity	NPD5217	Approved
0.6729	Remote Similarity	NPD5216	Approved
0.6727	Remote Similarity	NPD7115	Discovery
0.6705	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD8028	Phase 2
0.6699	Remote Similarity	NPD6052	Approved
0.6696	Remote Similarity	NPD6319	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD6101	Approved
0.6637	Remote Similarity	NPD5983	Phase 2
0.6637	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4225	Approved
0.6628	Remote Similarity	NPD4243	Approved
0.6627	Remote Similarity	NPD3704	Approved
0.6604	Remote Similarity	NPD6686	Approved
0.6591	Remote Similarity	NPD7339	Approved
0.6591	Remote Similarity	NPD6942	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