NPASS Compound

Structure

NPC476046 OpenBabel07101719152D 22 24 0 0 1 0 0 0 0 0999 V2000 4.6888 4.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2575 2.3912 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7229 3.9659 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 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 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 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 3 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 0.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 2 0 0 0 0 5 18 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 9 12 1 0 0 0 0 9 15 2 0 0 0 0 10 19 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 20 1 0 0 0 0 17 21 2 0 0 0 0 17 22 1 0 0 0 0 18 2 1 6 0 0 0 19 3 1 6 0 0 0 20 4 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	302.22
Volume:	338.478
LogP:	4.606
LogD:	3.596
LogS:	-4.73
# Rotatable Bonds:	2
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.711
Synthetic Accessibility Score:	4.401
Fsp3:	0.75
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:	-4.866
MDCK Permeability:	1.8594657376524992e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.869
30% Bioavailability (F30%):	0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.717
Plasma Protein Binding (PPB):	95.54717254638672%
Volume Distribution (VD):	0.775
Pgp-substrate:	4.834493160247803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.02
CYP1A2-substrate:	0.443
CYP2C19-inhibitor:	0.023
CYP2C19-substrate:	0.863
CYP2C9-inhibitor:	0.136
CYP2C9-substrate:	0.235
CYP2D6-inhibitor:	0.013
CYP2D6-substrate:	0.159
CYP3A4-inhibitor:	0.636
CYP3A4-substrate:	0.237

ADMET: Excretion

Clearance (CL):	1.1
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.361
Drug-inuced Liver Injury (DILI):	0.023
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.07
Maximum Recommended Daily Dose:	0.63
Skin Sensitization:	0.207
Carcinogencity:	0.382
Eye Corrosion:	0.3
Eye Irritation:	0.568
Respiratory Toxicity:	0.917

Download Data

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

Natural Product: NPC476046

Natural Product ID:	NPC476046
*Common Name:**	(1R,4Ar,7R,10As)-7-Ethenyl-1,4A,7-Trimethyl-3,4,6,8,8A,9,10,10A-Octahydro-2H-Phenanthrene-1-Carboxylic Acid
IUPAC Name:	(1R,4aR,7R,10aS)-7-ethenyl-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	TVHDZSRRHQKNEZ-STWDSKMCSA-N
Standard InCHI:	InChI=1S/C20H30O2/c1-5-18(2)12-9-15-14(13-18)7-8-16-19(15,3)10-6-11-20(16,4)17(21)22/h5,9,14,16H,1,6-8,10-13H2,2-4H3,(H,21,22)/t14?,16-,18+,19-,20+/m0/s1
SMILES:	C=C[C@]1(C)CC=C2C(C1)CC[C@H]1[C@@]2(C)CCC[C@@]1(C)C(=O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL523295
PubChem CID:	44566222
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO33152	calceolaria pinifolia	Species	Calceolariaceae	Eukaryota	aerial part	46 km west of Puesto de Gendarmeria in the province of San Juan, Argentina (3021 S; 6940 W)	1997-Jan	PMID[12608857]

☑ 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
MIC	4

Activity Type	# Activity
Organism	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	32.0	ug.mL-1	PMID[528910]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	16.0	ug.mL-1	PMID[528910]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	32.0	ug.mL-1	PMID[528910]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	128.0	ug.mL-1	PMID[528910]

☑ 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 NPC476046 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	159
0.1-0.2	1090
0.2-0.3	5974
0.3-0.4	16330
0.4-0.5	7941
0.5-0.6	6156
0.6-0.7	3682
0.7-0.8	1184
0.8-0.85	115
0.85-0.9	42
0.9-0.95	13
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC251970
1.0	High Similarity	NPC241854
0.9855	High Similarity	NPC279666
0.9855	High Similarity	NPC192540
0.9714	High Similarity	NPC69143
0.971	High Similarity	NPC161923
0.971	High Similarity	NPC103958
0.971	High Similarity	NPC283908
0.971	High Similarity	NPC183503
0.942	High Similarity	NPC160817
0.9306	High Similarity	NPC471899
0.9306	High Similarity	NPC471897
0.9306	High Similarity	NPC107039
0.9178	High Similarity	NPC280654
0.9178	High Similarity	NPC110094
0.9178	High Similarity	NPC260385
0.9167	High Similarity	NPC309399
0.9167	High Similarity	NPC89294
0.9155	High Similarity	NPC237591
0.9155	High Similarity	NPC3753
0.9054	High Similarity	NPC199595
0.9054	High Similarity	NPC231431
0.9054	High Similarity	NPC16394
0.9041	High Similarity	NPC165711
0.9028	High Similarity	NPC476844
0.9028	High Similarity	NPC201027
0.8933	High Similarity	NPC104545
0.8933	High Similarity	NPC37038
0.8919	High Similarity	NPC179028
0.8904	High Similarity	NPC180886
0.8889	High Similarity	NPC166797
0.8889	High Similarity	NPC301065
0.8816	High Similarity	NPC471898
0.8816	High Similarity	NPC263272
0.8816	High Similarity	NPC267691
0.8816	High Similarity	NPC278459
0.8816	High Similarity	NPC142244
0.8816	High Similarity	NPC274050
0.8816	High Similarity	NPC162632
0.8816	High Similarity	NPC221647
0.8816	High Similarity	NPC147066
0.8767	High Similarity	NPC476795
0.8701	High Similarity	NPC251779
0.8701	High Similarity	NPC69101
0.8701	High Similarity	NPC320514
0.8701	High Similarity	NPC238991
0.8701	High Similarity	NPC302661
0.8684	High Similarity	NPC26139
0.8684	High Similarity	NPC477057
0.8667	High Similarity	NPC321514
0.863	High Similarity	NPC255168
0.8608	High Similarity	NPC474537
0.8608	High Similarity	NPC29447
0.859	High Similarity	NPC477852
0.859	High Similarity	NPC200752
0.859	High Similarity	NPC70834
0.859	High Similarity	NPC167103
0.8571	High Similarity	NPC38350
0.8571	High Similarity	NPC201912
0.8553	High Similarity	NPC327674
0.8553	High Similarity	NPC477371
0.8553	High Similarity	NPC158846
0.8533	High Similarity	NPC472300
0.8533	High Similarity	NPC61952
0.85	High Similarity	NPC82979
0.8493	Intermediate Similarity	NPC330659
0.8493	Intermediate Similarity	NPC35656
0.8493	Intermediate Similarity	NPC36310
0.8493	Intermediate Similarity	NPC161187
0.8493	Intermediate Similarity	NPC244708
0.8481	Intermediate Similarity	NPC96095
0.8481	Intermediate Similarity	NPC477289
0.8481	Intermediate Similarity	NPC156981
0.8462	Intermediate Similarity	NPC260956
0.8462	Intermediate Similarity	NPC73882
0.8451	Intermediate Similarity	NPC290445
0.8451	Intermediate Similarity	NPC36616
0.8442	Intermediate Similarity	NPC476809
0.8421	Intermediate Similarity	NPC59436
0.8421	Intermediate Similarity	NPC239098
0.8421	Intermediate Similarity	NPC74410
0.8421	Intermediate Similarity	NPC198240
0.84	Intermediate Similarity	NPC899
0.8378	Intermediate Similarity	NPC18819
0.8378	Intermediate Similarity	NPC46610
0.8375	Intermediate Similarity	NPC76333
0.8354	Intermediate Similarity	NPC215893
0.8354	Intermediate Similarity	NPC83569
0.8354	Intermediate Similarity	NPC102197
0.8354	Intermediate Similarity	NPC105803
0.8354	Intermediate Similarity	NPC69279
0.8333	Intermediate Similarity	NPC473420
0.8333	Intermediate Similarity	NPC327002
0.8333	Intermediate Similarity	NPC477372
0.8312	Intermediate Similarity	NPC192329
0.8312	Intermediate Similarity	NPC474113
0.8289	Intermediate Similarity	NPC97377
0.8272	Intermediate Similarity	NPC325594
0.8272	Intermediate Similarity	NPC155011
0.8272	Intermediate Similarity	NPC324063
0.8272	Intermediate Similarity	NPC73038
0.825	Intermediate Similarity	NPC248758
0.8243	Intermediate Similarity	NPC177826
0.8228	Intermediate Similarity	NPC133391
0.8219	Intermediate Similarity	NPC91369
0.8219	Intermediate Similarity	NPC235586
0.8205	Intermediate Similarity	NPC267517
0.8205	Intermediate Similarity	NPC472478
0.8205	Intermediate Similarity	NPC2482
0.8193	Intermediate Similarity	NPC262043
0.8182	Intermediate Similarity	NPC471409
0.8182	Intermediate Similarity	NPC189485
0.8182	Intermediate Similarity	NPC4827
0.8182	Intermediate Similarity	NPC275494
0.8171	Intermediate Similarity	NPC88716
0.8171	Intermediate Similarity	NPC173089
0.8171	Intermediate Similarity	NPC307426
0.8171	Intermediate Similarity	NPC68160
0.8171	Intermediate Similarity	NPC51700
0.8171	Intermediate Similarity	NPC102683
0.8171	Intermediate Similarity	NPC71507
0.8171	Intermediate Similarity	NPC474684
0.8171	Intermediate Similarity	NPC136948
0.8171	Intermediate Similarity	NPC18064
0.8171	Intermediate Similarity	NPC293564
0.8171	Intermediate Similarity	NPC98442
0.8171	Intermediate Similarity	NPC142361
0.8171	Intermediate Similarity	NPC171203
0.8171	Intermediate Similarity	NPC158141
0.8171	Intermediate Similarity	NPC130577
0.8171	Intermediate Similarity	NPC242468
0.8171	Intermediate Similarity	NPC142415
0.8171	Intermediate Similarity	NPC96496
0.8158	Intermediate Similarity	NPC104806
0.8158	Intermediate Similarity	NPC246445
0.8148	Intermediate Similarity	NPC474680
0.8148	Intermediate Similarity	NPC269638
0.8143	Intermediate Similarity	NPC469662
0.8143	Intermediate Similarity	NPC234767
0.8133	Intermediate Similarity	NPC306928
0.8133	Intermediate Similarity	NPC213223
0.8125	Intermediate Similarity	NPC49019
0.8125	Intermediate Similarity	NPC312480
0.8125	Intermediate Similarity	NPC168188
0.8125	Intermediate Similarity	NPC97913
0.8125	Intermediate Similarity	NPC477373
0.8125	Intermediate Similarity	NPC470015
0.8108	Intermediate Similarity	NPC72343
0.8101	Intermediate Similarity	NPC121984
0.8101	Intermediate Similarity	NPC229584
0.8101	Intermediate Similarity	NPC474955
0.8101	Intermediate Similarity	NPC40228
0.8101	Intermediate Similarity	NPC14203
0.8101	Intermediate Similarity	NPC90055
0.8101	Intermediate Similarity	NPC3915
0.8101	Intermediate Similarity	NPC14151
0.8077	Intermediate Similarity	NPC215843
0.8077	Intermediate Similarity	NPC196827
0.8077	Intermediate Similarity	NPC274996
0.8072	Intermediate Similarity	NPC48107
0.8072	Intermediate Similarity	NPC17733
0.8072	Intermediate Similarity	NPC40552
0.8072	Intermediate Similarity	NPC52169
0.8072	Intermediate Similarity	NPC473242
0.8072	Intermediate Similarity	NPC474474
0.8072	Intermediate Similarity	NPC470629
0.8072	Intermediate Similarity	NPC290690
0.8072	Intermediate Similarity	NPC181225
0.8072	Intermediate Similarity	NPC182797
0.8072	Intermediate Similarity	NPC474512
0.8072	Intermediate Similarity	NPC474511
0.8072	Intermediate Similarity	NPC246708
0.8072	Intermediate Similarity	NPC1753
0.8052	Intermediate Similarity	NPC66105
0.8052	Intermediate Similarity	NPC68828
0.8052	Intermediate Similarity	NPC212661
0.8052	Intermediate Similarity	NPC471035
0.8049	Intermediate Similarity	NPC72638
0.8049	Intermediate Similarity	NPC322159
0.8049	Intermediate Similarity	NPC262085
0.8026	Intermediate Similarity	NPC476346
0.8025	Intermediate Similarity	NPC164577
0.8025	Intermediate Similarity	NPC472864
0.8025	Intermediate Similarity	NPC472865
0.8025	Intermediate Similarity	NPC165064
0.8025	Intermediate Similarity	NPC194937
0.8025	Intermediate Similarity	NPC19849
0.8025	Intermediate Similarity	NPC476038
0.8	Intermediate Similarity	NPC151519
0.8	Intermediate Similarity	NPC202118
0.8	Intermediate Similarity	NPC197238
0.8	Intermediate Similarity	NPC56747
0.8	Intermediate Similarity	NPC472813
0.8	Intermediate Similarity	NPC109576
0.8	Intermediate Similarity	NPC301244
0.8	Intermediate Similarity	NPC193347
0.8	Intermediate Similarity	NPC180015
0.8	Intermediate Similarity	NPC130016
0.8	Intermediate Similarity	NPC310989
0.7976	Intermediate Similarity	NPC225585

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 NPC476046 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1456
0.2-0.3	3925
0.3-0.4	2429
0.4-0.5	684
0.5-0.6	230
0.6-0.7	194
0.7-0.8	71
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD3667	Approved
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.7975	Intermediate Similarity	NPD4695	Discontinued
0.7831	Intermediate Similarity	NPD4519	Discontinued
0.7831	Intermediate Similarity	NPD4623	Approved
0.7805	Intermediate Similarity	NPD4786	Approved
0.7805	Intermediate Similarity	NPD3133	Approved
0.7805	Intermediate Similarity	NPD4197	Approved
0.7805	Intermediate Similarity	NPD3666	Approved
0.7805	Intermediate Similarity	NPD3665	Phase 1
0.7791	Intermediate Similarity	NPD7515	Phase 2
0.7791	Intermediate Similarity	NPD5281	Approved
0.7791	Intermediate Similarity	NPD5284	Approved
0.7765	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD3573	Approved
0.7722	Intermediate Similarity	NPD3617	Approved
0.7711	Intermediate Similarity	NPD5329	Approved
0.7701	Intermediate Similarity	NPD6399	Phase 3
0.7619	Intermediate Similarity	NPD5205	Approved
0.7619	Intermediate Similarity	NPD6098	Approved
0.7619	Intermediate Similarity	NPD4690	Approved
0.7619	Intermediate Similarity	NPD7146	Approved
0.7619	Intermediate Similarity	NPD4688	Approved
0.7619	Intermediate Similarity	NPD4138	Approved
0.7619	Intermediate Similarity	NPD7521	Approved
0.7619	Intermediate Similarity	NPD7334	Approved
0.7619	Intermediate Similarity	NPD4693	Phase 3
0.7619	Intermediate Similarity	NPD6684	Approved
0.7619	Intermediate Similarity	NPD5690	Phase 2
0.7619	Intermediate Similarity	NPD3618	Phase 1
0.7619	Intermediate Similarity	NPD6409	Approved
0.7619	Intermediate Similarity	NPD4689	Approved
0.7619	Intermediate Similarity	NPD5330	Approved
0.7614	Intermediate Similarity	NPD7748	Approved
0.76	Intermediate Similarity	NPD4137	Phase 3
0.75	Intermediate Similarity	NPD4747	Approved
0.75	Intermediate Similarity	NPD4691	Approved
0.7467	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD6903	Approved
0.7442	Intermediate Similarity	NPD5208	Approved
0.7442	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD5737	Approved
0.7442	Intermediate Similarity	NPD6672	Approved
0.7436	Intermediate Similarity	NPD4058	Approved
0.7412	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5280	Approved
0.7412	Intermediate Similarity	NPD4694	Approved
0.7407	Intermediate Similarity	NPD4195	Approved
0.7386	Intermediate Similarity	NPD6079	Approved
0.7381	Intermediate Similarity	NPD3668	Phase 3
0.7363	Intermediate Similarity	NPD6084	Phase 2
0.7363	Intermediate Similarity	NPD6083	Phase 2
0.7363	Intermediate Similarity	NPD7902	Approved
0.7356	Intermediate Similarity	NPD6904	Approved
0.7356	Intermediate Similarity	NPD6080	Approved
0.7356	Intermediate Similarity	NPD6673	Approved
0.7356	Intermediate Similarity	NPD4753	Phase 2
0.7356	Intermediate Similarity	NPD5328	Approved
0.7349	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5695	Phase 3
0.7294	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD5696	Approved
0.7273	Intermediate Similarity	NPD5207	Approved
0.7253	Intermediate Similarity	NPD7614	Phase 1
0.7229	Intermediate Similarity	NPD4692	Approved
0.7229	Intermediate Similarity	NPD4139	Approved
0.7215	Intermediate Similarity	NPD4785	Approved
0.7215	Intermediate Similarity	NPD4687	Approved
0.7215	Intermediate Similarity	NPD4784	Approved
0.7209	Intermediate Similarity	NPD5279	Phase 3
0.7206	Intermediate Similarity	NPD3172	Approved
0.72	Intermediate Similarity	NPD4224	Phase 2
0.7191	Intermediate Similarity	NPD6411	Approved
0.7191	Intermediate Similarity	NPD5693	Phase 1
0.7191	Intermediate Similarity	NPD5694	Approved
0.7179	Intermediate Similarity	NPD4243	Approved
0.7143	Intermediate Similarity	NPD5210	Approved
0.7143	Intermediate Similarity	NPD4629	Approved
0.7125	Intermediate Similarity	NPD8039	Approved
0.7111	Intermediate Similarity	NPD4202	Approved
0.7101	Intermediate Similarity	NPD4266	Approved
0.7101	Intermediate Similarity	NPD3195	Phase 2
0.7101	Intermediate Similarity	NPD3196	Approved
0.7101	Intermediate Similarity	NPD3194	Approved
0.7079	Intermediate Similarity	NPD5692	Phase 3
0.7065	Intermediate Similarity	NPD5222	Approved
0.7065	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD5221	Approved
0.7037	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD7900	Approved
0.7033	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6001	Approved
0.7021	Intermediate Similarity	NPD6404	Discontinued
0.7	Intermediate Similarity	NPD5733	Approved
0.7	Intermediate Similarity	NPD6050	Approved
0.6989	Remote Similarity	NPD5173	Approved
0.6974	Remote Similarity	NPD7331	Phase 2
0.6966	Remote Similarity	NPD6101	Approved
0.6966	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5276	Approved
0.6957	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD5697	Approved
0.6914	Remote Similarity	NPD5275	Approved
0.6914	Remote Similarity	NPD4190	Phase 3
0.6914	Remote Similarity	NPD6942	Approved
0.6914	Remote Similarity	NPD7339	Approved
0.6889	Remote Similarity	NPD4096	Approved
0.6882	Remote Similarity	NPD4697	Phase 3
0.6869	Remote Similarity	NPD6011	Approved
0.6869	Remote Similarity	NPD6899	Approved
0.6869	Remote Similarity	NPD6881	Approved
0.6867	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.686	Remote Similarity	NPD4788	Approved
0.6854	Remote Similarity	NPD4518	Approved
0.6842	Remote Similarity	NPD5286	Approved
0.6842	Remote Similarity	NPD4696	Approved
0.6842	Remote Similarity	NPD5285	Approved
0.6837	Remote Similarity	NPD5739	Approved
0.6837	Remote Similarity	NPD6675	Approved
0.6837	Remote Similarity	NPD6402	Approved
0.6837	Remote Similarity	NPD7128	Approved
0.6813	Remote Similarity	NPD8034	Phase 2
0.6813	Remote Similarity	NPD8035	Phase 2
0.6809	Remote Similarity	NPD4755	Approved
0.68	Remote Similarity	NPD6012	Approved
0.68	Remote Similarity	NPD6014	Approved
0.68	Remote Similarity	NPD6013	Approved
0.6786	Remote Similarity	NPD7645	Phase 2
0.6771	Remote Similarity	NPD5223	Approved
0.6768	Remote Similarity	NPD5701	Approved
0.675	Remote Similarity	NPD6081	Approved
0.6739	Remote Similarity	NPD5133	Approved
0.6737	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD7102	Approved
0.6733	Remote Similarity	NPD6883	Approved
0.6733	Remote Similarity	NPD7290	Approved
0.6705	Remote Similarity	NPD1694	Approved
0.6702	Remote Similarity	NPD7732	Phase 3
0.6701	Remote Similarity	NPD5091	Approved
0.6701	Remote Similarity	NPD4633	Approved
0.6701	Remote Similarity	NPD5224	Approved
0.6701	Remote Similarity	NPD5211	Phase 2
0.6701	Remote Similarity	NPD5226	Approved
0.6701	Remote Similarity	NPD5225	Approved
0.67	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD4192	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD28	Approved
0.6667	Remote Similarity	NPD6869	Approved
0.6667	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD6649	Approved
0.6667	Remote Similarity	NPD4194	Approved
0.6667	Remote Similarity	NPD6847	Approved
0.6667	Remote Similarity	NPD29	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6650	Approved
0.6667	Remote Similarity	NPD4193	Approved
0.6667	Remote Similarity	NPD4191	Approved
0.6667	Remote Similarity	NPD6617	Approved
0.6634	Remote Similarity	NPD6373	Approved
0.6634	Remote Similarity	NPD6372	Approved
0.6633	Remote Similarity	NPD5174	Approved
0.6633	Remote Similarity	NPD5175	Approved
0.6628	Remote Similarity	NPD857	Phase 3
0.6623	Remote Similarity	NPD7341	Phase 2
0.6618	Remote Similarity	NPD3173	Approved
0.6602	Remote Similarity	NPD6882	Approved
0.6602	Remote Similarity	NPD8297	Approved
0.6596	Remote Similarity	NPD5654	Approved
0.6585	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD5141	Approved
0.6559	Remote Similarity	NPD1088	Approved
0.6559	Remote Similarity	NPD5778	Approved
0.6559	Remote Similarity	NPD5779	Approved
0.6538	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD5368	Approved
0.6512	Remote Similarity	NPD7525	Registered
0.6506	Remote Similarity	NPD3702	Approved
0.6505	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD287	Approved
0.6477	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6477	Remote Similarity	NPD5362	Discontinued
0.6471	Remote Similarity	NPD622	Approved
0.6465	Remote Similarity	NPD6052	Approved
0.6465	Remote Similarity	NPD4754	Approved
0.6458	Remote Similarity	NPD5959	Approved
0.6452	Remote Similarity	NPD7637	Suspended
0.6437	Remote Similarity	NPD5369	Approved
0.6437	Remote Similarity	NPD8028	Phase 2
0.6436	Remote Similarity	NPD6412	Phase 2
0.6436	Remote Similarity	NPD6614	Approved
0.6429	Remote Similarity	NPD6117	Approved
0.642	Remote Similarity	NPD7143	Approved
0.642	Remote Similarity	NPD7144	Approved
0.6415	Remote Similarity	NPD6868	Approved
0.6413	Remote Similarity	NPD6051	Approved
0.641	Remote Similarity	NPD3171	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