NPASS Compound

Structure

NPC179028 OpenBabel07101719512D 23 24 0 0 1 0 0 0 0 0999 V2000 -3.4744 -5.1566 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 -2.5085 -2.9659 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6559 -2.3827 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 -2.5085 -4.8978 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 -0.0000 -2.0000 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 -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 -1.2838 -3.6730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0249 -2.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 2 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 -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 -2.2497 -3.9319 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 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 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 -3.2156 -3.6730 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 14 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 11 1 0 0 0 0 8 15 2 0 0 0 0 9 10 1 0 0 0 0 9 14 1 0 0 0 0 10 16 1 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 18 1 0 0 0 0 13 19 1 0 0 0 0 14 19 1 6 0 0 0 15 16 1 0 0 0 0 15 19 1 0 0 0 0 16 20 1 6 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 3 1 1 0 0 0 18 23 1 0 0 0 0 19 4 1 6 0 0 0 20 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	355.825
LogP:	4.183
LogD:	3.411
LogS:	-3.922
# Rotatable Bonds:	5
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.73
Synthetic Accessibility Score:	4.73
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:	-4.987
MDCK Permeability:	1.7797990949475206e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.015
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.201
Plasma Protein Binding (PPB):	90.40074920654297%
Volume Distribution (VD):	0.643
Pgp-substrate:	13.112686157226562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.333
CYP2C19-inhibitor:	0.024
CYP2C19-substrate:	0.798
CYP2C9-inhibitor:	0.069
CYP2C9-substrate:	0.43
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.628
CYP3A4-substrate:	0.248

ADMET: Excretion

Clearance (CL):	1.601
Half-life (T1/2):	0.235

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.211
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.461
Maximum Recommended Daily Dose:	0.334
Skin Sensitization:	0.356
Carcinogencity:	0.82
Eye Corrosion:	0.988
Eye Irritation:	0.83
Respiratory Toxicity:	0.969

Download Data

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

Natural Product: NPC179028

Natural Product ID:	NPC179028
*Common Name:**	(13R)-13-Hydroxy-1(10),14-Ent-Halimadien-18-Oic Acid
IUPAC Name:	(1S,5S,6R,8aS)-5-[(3R)-3-hydroxy-3-methylpent-4-enyl]-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylic acid
Synonyms:
Standard InCHIKey:	LRUXWKFVLKWKRF-KXAOQFNBSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-6-18(3,23)12-13-19(4)14(2)9-10-16-15(19)8-7-11-20(16,5)17(21)22/h6,8,14,16,23H,1,7,9-13H2,2-5H3,(H,21,22)/t14-,16+,18+,19+,20+/m1/s1
SMILES:	C=C[C@@](C)(CC[C@@]1(C)[C@H](C)CC[C@H]2C1=CCC[C@]2(C)C(=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL508851
PubChem CID:	637420
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001670] Tertiary alcohols

*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
NPO1766	Hymenaea courbaril	Species	Fabaceae	Eukaryota	n.a.	Suriname rain forest	n.a.	PMID[11809056]
NPO1766	Hymenaea courbaril	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Cell Line	1
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT179	Cell Line	A2780	Homo sapiens	IC50	>	40.0	ug.mL-1	PMID[507992]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	925.0	ug ml-1	PMID[507992]

☑ 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 NPC179028 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	153
0.1-0.2	1031
0.2-0.3	5094
0.3-0.4	15045
0.4-0.5	9233
0.5-0.6	6699
0.6-0.7	4048
0.7-0.8	1230
0.8-0.85	111
0.85-0.9	45
0.9-0.95	7
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.92	High Similarity	NPC321514
0.92	High Similarity	NPC471409
0.92	High Similarity	NPC275494
0.9178	High Similarity	NPC18819
0.9178	High Similarity	NPC46610
0.9167	High Similarity	NPC160817
0.9079	High Similarity	NPC231431
0.9054	High Similarity	NPC476795
0.9054	High Similarity	NPC279666
0.9054	High Similarity	NPC192540
0.8961	High Similarity	NPC37038
0.8933	High Similarity	NPC69143
0.8919	High Similarity	NPC161923
0.8919	High Similarity	NPC241854
0.8919	High Similarity	NPC103958
0.8919	High Similarity	NPC476046
0.8919	High Similarity	NPC283908
0.8919	High Similarity	NPC183503
0.8919	High Similarity	NPC251970
0.8875	High Similarity	NPC269638
0.8846	High Similarity	NPC327002
0.8846	High Similarity	NPC142244
0.8831	High Similarity	NPC477371
0.8816	High Similarity	NPC107039
0.8816	High Similarity	NPC97377
0.8816	High Similarity	NPC471897
0.8816	High Similarity	NPC471899
0.88	High Similarity	NPC476844
0.8784	High Similarity	NPC35656
0.875	High Similarity	NPC165064
0.8701	High Similarity	NPC280654
0.8701	High Similarity	NPC239098
0.8701	High Similarity	NPC260385
0.8701	High Similarity	NPC110094
0.8684	High Similarity	NPC309399
0.8684	High Similarity	NPC89294
0.8684	High Similarity	NPC180886
0.8675	High Similarity	NPC262043
0.8667	High Similarity	NPC301065
0.8667	High Similarity	NPC237591
0.8667	High Similarity	NPC3753
0.8659	High Similarity	NPC128644
0.8659	High Similarity	NPC136948
0.8625	High Similarity	NPC477373
0.8625	High Similarity	NPC97913
0.8625	High Similarity	NPC310470
0.8608	High Similarity	NPC38350
0.8608	High Similarity	NPC278459
0.8608	High Similarity	NPC201912
0.8608	High Similarity	NPC477372
0.8608	High Similarity	NPC162632
0.8608	High Similarity	NPC471898
0.8608	High Similarity	NPC263272
0.8608	High Similarity	NPC274050
0.8608	High Similarity	NPC267691
0.8608	High Similarity	NPC147066
0.859	High Similarity	NPC199595
0.859	High Similarity	NPC327674
0.859	High Similarity	NPC16394
0.8571	High Similarity	NPC257666
0.8571	High Similarity	NPC165711
0.8571	High Similarity	NPC266193
0.8571	High Similarity	NPC61952
0.8537	High Similarity	NPC82979
0.8537	High Similarity	NPC472869
0.8519	High Similarity	NPC472865
0.8519	High Similarity	NPC164577
0.8519	High Similarity	NPC156981
0.85	High Similarity	NPC251779
0.85	High Similarity	NPC260956
0.85	High Similarity	NPC69101
0.85	High Similarity	NPC133391
0.8481	Intermediate Similarity	NPC104545
0.8472	Intermediate Similarity	NPC279434
0.8471	Intermediate Similarity	NPC204341
0.8462	Intermediate Similarity	NPC198240
0.8462	Intermediate Similarity	NPC74410
0.8452	Intermediate Similarity	NPC36668
0.8452	Intermediate Similarity	NPC118011
0.8434	Intermediate Similarity	NPC171722
0.8434	Intermediate Similarity	NPC476409
0.8421	Intermediate Similarity	NPC166797
0.8415	Intermediate Similarity	NPC474537
0.8415	Intermediate Similarity	NPC29447
0.8395	Intermediate Similarity	NPC477852
0.8395	Intermediate Similarity	NPC83569
0.8395	Intermediate Similarity	NPC70834
0.8395	Intermediate Similarity	NPC49019
0.8395	Intermediate Similarity	NPC69279
0.8375	Intermediate Similarity	NPC221647
0.8375	Intermediate Similarity	NPC473420
0.8354	Intermediate Similarity	NPC158846
0.8333	Intermediate Similarity	NPC117122
0.8333	Intermediate Similarity	NPC48107
0.8333	Intermediate Similarity	NPC132542
0.8333	Intermediate Similarity	NPC72397
0.8333	Intermediate Similarity	NPC472870
0.8313	Intermediate Similarity	NPC473226
0.8313	Intermediate Similarity	NPC239685
0.8313	Intermediate Similarity	NPC262085
0.8313	Intermediate Similarity	NPC322159
0.8313	Intermediate Similarity	NPC324063
0.8313	Intermediate Similarity	NPC73038
0.8312	Intermediate Similarity	NPC201027
0.8312	Intermediate Similarity	NPC39362
0.8312	Intermediate Similarity	NPC476346
0.8293	Intermediate Similarity	NPC19849
0.8293	Intermediate Similarity	NPC476038
0.8293	Intermediate Similarity	NPC194937
0.8293	Intermediate Similarity	NPC472864
0.8293	Intermediate Similarity	NPC96095
0.8289	Intermediate Similarity	NPC180015
0.8289	Intermediate Similarity	NPC130016
0.8289	Intermediate Similarity	NPC109576
0.8289	Intermediate Similarity	NPC56747
0.8272	Intermediate Similarity	NPC73882
0.8272	Intermediate Similarity	NPC238991
0.8272	Intermediate Similarity	NPC302661
0.8272	Intermediate Similarity	NPC320514
0.8267	Intermediate Similarity	NPC235586
0.825	Intermediate Similarity	NPC476809
0.825	Intermediate Similarity	NPC477057
0.825	Intermediate Similarity	NPC26139
0.8243	Intermediate Similarity	NPC36616
0.8243	Intermediate Similarity	NPC290445
0.8235	Intermediate Similarity	NPC281524
0.8228	Intermediate Similarity	NPC297996
0.8228	Intermediate Similarity	NPC269543
0.8228	Intermediate Similarity	NPC247783
0.8214	Intermediate Similarity	NPC231599
0.8214	Intermediate Similarity	NPC236618
0.8205	Intermediate Similarity	NPC104806
0.8205	Intermediate Similarity	NPC899
0.8205	Intermediate Similarity	NPC472305
0.8205	Intermediate Similarity	NPC263582
0.8193	Intermediate Similarity	NPC471344
0.8193	Intermediate Similarity	NPC283733
0.8182	Intermediate Similarity	NPC213223
0.8182	Intermediate Similarity	NPC306928
0.8182	Intermediate Similarity	NPC255168
0.8171	Intermediate Similarity	NPC167103
0.8171	Intermediate Similarity	NPC215893
0.8171	Intermediate Similarity	NPC200752
0.8148	Intermediate Similarity	NPC229584
0.8148	Intermediate Similarity	NPC14203
0.8148	Intermediate Similarity	NPC40228
0.814	Intermediate Similarity	NPC472866
0.814	Intermediate Similarity	NPC469400
0.8125	Intermediate Similarity	NPC196827
0.8125	Intermediate Similarity	NPC274996
0.8125	Intermediate Similarity	NPC215843
0.8118	Intermediate Similarity	NPC24816
0.8101	Intermediate Similarity	NPC472300
0.8101	Intermediate Similarity	NPC66105
0.8101	Intermediate Similarity	NPC137547
0.8101	Intermediate Similarity	NPC325946
0.8101	Intermediate Similarity	NPC34110
0.8101	Intermediate Similarity	NPC74995
0.8095	Intermediate Similarity	NPC476982
0.8095	Intermediate Similarity	NPC325594
0.8095	Intermediate Similarity	NPC155011
0.8095	Intermediate Similarity	NPC476104
0.8095	Intermediate Similarity	NPC186975
0.8072	Intermediate Similarity	NPC476412
0.8072	Intermediate Similarity	NPC477289
0.8072	Intermediate Similarity	NPC248758
0.8052	Intermediate Similarity	NPC36310
0.8052	Intermediate Similarity	NPC247586
0.8052	Intermediate Similarity	NPC177826
0.8046	Intermediate Similarity	NPC473986
0.8046	Intermediate Similarity	NPC474018
0.8026	Intermediate Similarity	NPC91369
0.8025	Intermediate Similarity	NPC267517
0.8025	Intermediate Similarity	NPC306095
0.8025	Intermediate Similarity	NPC2482
0.8025	Intermediate Similarity	NPC271104
0.8023	Intermediate Similarity	NPC2983
0.8023	Intermediate Similarity	NPC66344
0.8023	Intermediate Similarity	NPC155479
0.8	Intermediate Similarity	NPC171203
0.8	Intermediate Similarity	NPC142361
0.8	Intermediate Similarity	NPC173089
0.8	Intermediate Similarity	NPC18064
0.8	Intermediate Similarity	NPC59436
0.8	Intermediate Similarity	NPC4827
0.8	Intermediate Similarity	NPC71507
0.8	Intermediate Similarity	NPC130577
0.8	Intermediate Similarity	NPC321690
0.8	Intermediate Similarity	NPC68160
0.8	Intermediate Similarity	NPC474684
0.8	Intermediate Similarity	NPC142415
0.8	Intermediate Similarity	NPC307426
0.8	Intermediate Similarity	NPC98442
0.8	Intermediate Similarity	NPC181327
0.8	Intermediate Similarity	NPC158141
0.8	Intermediate Similarity	NPC167877
0.8	Intermediate Similarity	NPC187376
0.8	Intermediate Similarity	NPC102683
0.8	Intermediate Similarity	NPC293564
0.8	Intermediate Similarity	NPC107243

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 NPC179028 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	154
0.1-0.2	1472
0.2-0.3	3815
0.3-0.4	2409
0.4-0.5	785
0.5-0.6	277
0.6-0.7	183
0.7-0.8	55
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
0.8095	Intermediate Similarity	NPD4623	Approved
0.8095	Intermediate Similarity	NPD4519	Discontinued
0.7841	Intermediate Similarity	NPD5284	Approved
0.7841	Intermediate Similarity	NPD5281	Approved
0.7831	Intermediate Similarity	NPD4221	Approved
0.7831	Intermediate Similarity	NPD4223	Phase 3
0.7765	Intermediate Similarity	NPD5329	Approved
0.7674	Intermediate Similarity	NPD5690	Phase 2
0.7674	Intermediate Similarity	NPD6098	Approved
0.7647	Intermediate Similarity	NPD4197	Approved
0.7647	Intermediate Similarity	NPD4786	Approved
0.764	Intermediate Similarity	NPD7515	Phase 2
0.7619	Intermediate Similarity	NPD3667	Approved
0.7614	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD4695	Discontinued
0.7586	Intermediate Similarity	NPD3573	Approved
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.7473	Intermediate Similarity	NPD7748	Approved
0.7471	Intermediate Similarity	NPD4688	Approved
0.7471	Intermediate Similarity	NPD4138	Approved
0.7471	Intermediate Similarity	NPD5205	Approved
0.7471	Intermediate Similarity	NPD7146	Approved
0.7471	Intermediate Similarity	NPD5280	Approved
0.7471	Intermediate Similarity	NPD4693	Phase 3
0.7471	Intermediate Similarity	NPD4690	Approved
0.7471	Intermediate Similarity	NPD7521	Approved
0.7471	Intermediate Similarity	NPD7334	Approved
0.7471	Intermediate Similarity	NPD4694	Approved
0.7471	Intermediate Similarity	NPD4689	Approved
0.7471	Intermediate Similarity	NPD6409	Approved
0.7471	Intermediate Similarity	NPD5330	Approved
0.7471	Intermediate Similarity	NPD6684	Approved
0.7442	Intermediate Similarity	NPD3665	Phase 1
0.7442	Intermediate Similarity	NPD3666	Approved
0.7442	Intermediate Similarity	NPD3133	Approved
0.7419	Intermediate Similarity	NPD6083	Phase 2
0.7419	Intermediate Similarity	NPD6084	Phase 2
0.7416	Intermediate Similarity	NPD6673	Approved
0.7416	Intermediate Similarity	NPD6904	Approved
0.7416	Intermediate Similarity	NPD6080	Approved
0.7391	Intermediate Similarity	NPD5695	Phase 3
0.7349	Intermediate Similarity	NPD3617	Approved
0.7349	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5207	Approved
0.7303	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6903	Approved
0.7303	Intermediate Similarity	NPD6672	Approved
0.7303	Intermediate Similarity	NPD5208	Approved
0.7303	Intermediate Similarity	NPD5737	Approved
0.7294	Intermediate Similarity	NPD4139	Approved
0.7294	Intermediate Similarity	NPD4692	Approved
0.7284	Intermediate Similarity	NPD4784	Approved
0.7284	Intermediate Similarity	NPD4785	Approved
0.7273	Intermediate Similarity	NPD7331	Phase 2
0.7273	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3618	Phase 1
0.7263	Intermediate Similarity	NPD6404	Discontinued
0.7262	Intermediate Similarity	NPD4195	Approved
0.7253	Intermediate Similarity	NPD6050	Approved
0.7253	Intermediate Similarity	NPD5694	Approved
0.7253	Intermediate Similarity	NPD6411	Approved
0.7253	Intermediate Similarity	NPD6079	Approved
0.7253	Intermediate Similarity	NPD5693	Phase 1
0.725	Intermediate Similarity	NPD4243	Approved
0.7234	Intermediate Similarity	NPD7902	Approved
0.7222	Intermediate Similarity	NPD5328	Approved
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD8039	Approved
0.7174	Intermediate Similarity	NPD5778	Approved
0.7174	Intermediate Similarity	NPD5779	Approved
0.7159	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD5696	Approved
0.7143	Intermediate Similarity	NPD5692	Phase 3
0.7143	Intermediate Similarity	NPD7341	Phase 2
0.7128	Intermediate Similarity	NPD7614	Phase 1
0.7079	Intermediate Similarity	NPD5279	Phase 3
0.7045	Intermediate Similarity	NPD3668	Phase 3
0.7033	Intermediate Similarity	NPD6101	Approved
0.7033	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD5210	Approved
0.7021	Intermediate Similarity	NPD4629	Approved
0.7021	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4137	Phase 3
0.6989	Remote Similarity	NPD4202	Approved
0.6966	Remote Similarity	NPD1694	Approved
0.6957	Remote Similarity	NPD4096	Approved
0.6944	Remote Similarity	NPD3195	Phase 2
0.6944	Remote Similarity	NPD3194	Approved
0.6944	Remote Similarity	NPD4266	Approved
0.6944	Remote Similarity	NPD3196	Approved
0.6939	Remote Similarity	NPD5211	Phase 2
0.6932	Remote Similarity	NPD5362	Discontinued
0.6932	Remote Similarity	NPD4788	Approved
0.6931	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6923	Remote Similarity	NPD4518	Approved
0.6915	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD7900	Approved
0.6915	Remote Similarity	NPD6001	Approved
0.6914	Remote Similarity	NPD4691	Approved
0.6914	Remote Similarity	NPD4747	Approved
0.6907	Remote Similarity	NPD7640	Approved
0.6907	Remote Similarity	NPD7639	Approved
0.69	Remote Similarity	NPD6402	Approved
0.69	Remote Similarity	NPD5739	Approved
0.69	Remote Similarity	NPD7128	Approved
0.69	Remote Similarity	NPD6675	Approved
0.6875	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD4687	Approved
0.6867	Remote Similarity	NPD5733	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.6835	Remote Similarity	NPD4224	Phase 2
0.6832	Remote Similarity	NPD5697	Approved
0.6818	Remote Similarity	NPD4270	Approved
0.6818	Remote Similarity	NPD4269	Approved
0.6809	Remote Similarity	NPD5133	Approved
0.6806	Remote Similarity	NPD3172	Approved
0.6804	Remote Similarity	NPD7638	Approved
0.68	Remote Similarity	NPD5141	Approved
0.6796	Remote Similarity	NPD7102	Approved
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.6786	Remote Similarity	NPD4190	Phase 3
0.6786	Remote Similarity	NPD5275	Approved
0.6786	Remote Similarity	NPD8264	Approved
0.6786	Remote Similarity	NPD7339	Approved
0.6786	Remote Similarity	NPD6942	Approved
0.6782	Remote Similarity	NPD4819	Approved
0.6782	Remote Similarity	NPD4821	Approved
0.6782	Remote Similarity	NPD4820	Approved
0.6782	Remote Similarity	NPD4822	Approved
0.6771	Remote Similarity	NPD5222	Approved
0.6771	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5221	Approved
0.6765	Remote Similarity	NPD7320	Approved
0.6765	Remote Similarity	NPD6011	Approved
0.6753	Remote Similarity	NPD4192	Approved
0.6753	Remote Similarity	NPD4193	Approved
0.6753	Remote Similarity	NPD4191	Approved
0.6753	Remote Similarity	NPD4194	Approved
0.6742	Remote Similarity	NPD7154	Phase 3
0.6735	Remote Similarity	NPD5285	Approved
0.6735	Remote Similarity	NPD5286	Approved
0.6735	Remote Similarity	NPD4696	Approved
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6706	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD5369	Approved
0.6702	Remote Similarity	NPD7637	Suspended
0.6702	Remote Similarity	NPD8035	Phase 2
0.6702	Remote Similarity	NPD8034	Phase 2
0.6701	Remote Similarity	NPD5173	Approved
0.6701	Remote Similarity	NPD4755	Approved
0.6699	Remote Similarity	NPD6014	Approved
0.6699	Remote Similarity	NPD6013	Approved
0.6699	Remote Similarity	NPD6373	Approved
0.6699	Remote Similarity	NPD6372	Approved
0.6699	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD5223	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD7645	Phase 2
0.6667	Remote Similarity	NPD6051	Approved
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5701	Approved
0.6667	Remote Similarity	NPD5654	Approved
0.6627	Remote Similarity	NPD6081	Approved
0.6627	Remote Similarity	NPD5276	Approved
0.66	Remote Similarity	NPD5091	Approved
0.66	Remote Similarity	NPD5225	Approved
0.66	Remote Similarity	NPD5224	Approved
0.66	Remote Similarity	NPD4633	Approved
0.66	Remote Similarity	NPD5226	Approved
0.6598	Remote Similarity	NPD4697	Phase 3
0.6598	Remote Similarity	NPD7732	Phase 3
0.6596	Remote Similarity	NPD5785	Approved
0.6593	Remote Similarity	NPD5363	Approved
0.6591	Remote Similarity	NPD4252	Approved
0.6591	Remote Similarity	NPD5368	Approved
0.6591	Remote Similarity	NPD6931	Approved
0.6591	Remote Similarity	NPD7525	Registered
0.6591	Remote Similarity	NPD6930	Phase 2
0.6571	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD4700	Approved
0.6556	Remote Similarity	NPD5332	Approved
0.6556	Remote Similarity	NPD5331	Approved
0.6552	Remote Similarity	NPD4271	Approved
0.6552	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD4268	Approved
0.6535	Remote Similarity	NPD6052	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6531	Remote Similarity	NPD5959	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