NPASS Compound

Structure

NPC291503 OpenBabel07101718312D 22 24 0 0 1 0 0 0 0 0999 V2000 4.2711 -1.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2321 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4676 -2.4914 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 3.5640 -1.2412 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 -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 -1.7321 1.0000 0.0000 C 0 0 0 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 2.5981 -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 1.7321 0.0000 0.0000 C 0 0 2 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 -0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 2 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 2.5981 -1.5000 0.0000 C 0 0 1 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 1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 10 1 0 0 0 0 9 16 1 0 0 0 0 10 18 1 0 0 0 0 11 13 2 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 19 1 0 0 0 0 13 17 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 6 0 0 0 15 18 1 0 0 0 0 15 20 1 1 0 0 0 16 20 1 6 0 0 0 16 22 1 0 0 0 0 17 20 1 1 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.946
LogD:	3.156
LogS:	-4.056
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.717
Synthetic Accessibility Score:	4.91
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.687
MDCK Permeability:	2.0070576283615083e-05
Pgp-inhibitor:	0.993
Pgp-substrate:	0.185
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.256
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.554
Plasma Protein Binding (PPB):	90.36582946777344%
Volume Distribution (VD):	1.511
Pgp-substrate:	12.478391647338867%

ADMET: Metabolism

CYP1A2-inhibitor:	0.036
CYP1A2-substrate:	0.258
CYP2C19-inhibitor:	0.068
CYP2C19-substrate:	0.799
CYP2C9-inhibitor:	0.146
CYP2C9-substrate:	0.191
CYP2D6-inhibitor:	0.019
CYP2D6-substrate:	0.099
CYP3A4-inhibitor:	0.815
CYP3A4-substrate:	0.353

ADMET: Excretion

Clearance (CL):	4.773
Half-life (T1/2):	0.364

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.04
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.887
Skin Sensitization:	0.146
Carcinogencity:	0.848
Eye Corrosion:	0.276
Eye Irritation:	0.117
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC291503

Natural Product ID:	NPC291503
*Common Name:**	(1S,5S,9S,10S,11R,13R)-1,11-Dihydroxypimara-8(14),15-Diene
IUPAC Name:	(4S,4aS,4bS,5R,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-4,5-diol
Synonyms:
Standard InCHIKey:	XSFKYBKBHXNLJA-ASZLNGMRSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-19(4)11-13-7-8-15-18(2,3)10-9-16(22)20(15,5)17(13)14(21)12-19/h6,11,14-17,21-22H,1,7-10,12H2,2-5H3/t14-,15+,16+,17-,19-,20-/m1/s1
SMILES:	C=C[C@@]1(C)C[C@@H](O)[C@H]2C(=C1)CC[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465366
PubChem CID:	11536804
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
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309313]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25919052]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31836445]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	Rhizomes	n.a.	n.a.	PMID[31873014]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22194	Kaempferia pulchra	Species	Zingiberaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29530	Kaempferia marginata	Species	Zingiberaceae	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	3
Others	8

Activity Type	# Activity
Cell Line	10
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	36700.0	nM	PMID[493186]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	13.38	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	6.28	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	46.6	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	50.35	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	95340.0	nM	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	78.37	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	86.73	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	35.86	%	PMID[493187]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	27.84	%	PMID[493187]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	3.2	ug.mL-1	PMID[493184]

☑ 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 NPC291503 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	175
0.1-0.2	1319
0.2-0.3	5557
0.3-0.4	15638
0.4-0.5	9190
0.5-0.6	5715
0.6-0.7	3611
0.7-0.8	1158
0.8-0.85	224
0.85-0.9	63
0.9-0.95	40
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9855	High Similarity	NPC243342
0.9855	High Similarity	NPC477138
0.9571	High Similarity	NPC91858
0.9565	High Similarity	NPC242001
0.9444	High Similarity	NPC471798
0.9437	High Similarity	NPC66566
0.9437	High Similarity	NPC477923
0.9429	High Similarity	NPC182717
0.9429	High Similarity	NPC471799
0.942	High Similarity	NPC145498
0.9324	High Similarity	NPC287749
0.9324	High Similarity	NPC96362
0.9306	High Similarity	NPC477925
0.9306	High Similarity	NPC274079
0.9306	High Similarity	NPC106432
0.9296	High Similarity	NPC471797
0.92	High Similarity	NPC476646
0.9178	High Similarity	NPC477924
0.9178	High Similarity	NPC91594
0.9155	High Similarity	NPC68443
0.9143	High Similarity	NPC92801
0.9054	High Similarity	NPC300499
0.9054	High Similarity	NPC22955
0.9054	High Similarity	NPC99168
0.9054	High Similarity	NPC474989
0.9054	High Similarity	NPC470396
0.9041	High Similarity	NPC265588
0.9028	High Similarity	NPC100334
0.9014	High Similarity	NPC110799
0.9014	High Similarity	NPC167706
0.8947	High Similarity	NPC142163
0.8933	High Similarity	NPC291379
0.8933	High Similarity	NPC53744
0.8919	High Similarity	NPC101475
0.8919	High Similarity	NPC40394
0.8919	High Similarity	NPC34177
0.8919	High Similarity	NPC472805
0.8919	High Similarity	NPC90979
0.8919	High Similarity	NPC157996
0.8919	High Similarity	NPC130136
0.8857	High Similarity	NPC208999
0.88	High Similarity	NPC476314
0.88	High Similarity	NPC167891
0.88	High Similarity	NPC244385
0.88	High Similarity	NPC98386
0.88	High Similarity	NPC167037
0.88	High Similarity	NPC158662
0.88	High Similarity	NPC138621
0.88	High Similarity	NPC83351
0.88	High Similarity	NPC275910
0.88	High Similarity	NPC196753
0.88	High Similarity	NPC230295
0.88	High Similarity	NPC6978
0.88	High Similarity	NPC253807
0.8784	High Similarity	NPC30590
0.8784	High Similarity	NPC321016
0.8784	High Similarity	NPC265328
0.8784	High Similarity	NPC134330
0.8784	High Similarity	NPC107059
0.8784	High Similarity	NPC129165
0.8784	High Similarity	NPC120098
0.8784	High Similarity	NPC253190
0.8784	High Similarity	NPC113733
0.8784	High Similarity	NPC106364
0.8784	High Similarity	NPC290598
0.8784	High Similarity	NPC27765
0.8784	High Similarity	NPC300324
0.8784	High Similarity	NPC189883
0.8784	High Similarity	NPC122418
0.8784	High Similarity	NPC321381
0.8784	High Similarity	NPC240604
0.875	High Similarity	NPC164022
0.8718	High Similarity	NPC237795
0.8718	High Similarity	NPC82538
0.8714	High Similarity	NPC197805
0.8701	High Similarity	NPC249423
0.8701	High Similarity	NPC474531
0.8684	High Similarity	NPC80530
0.8684	High Similarity	NPC472463
0.8684	High Similarity	NPC273410
0.8684	High Similarity	NPC100906
0.8684	High Similarity	NPC1319
0.8667	High Similarity	NPC470711
0.8667	High Similarity	NPC470758
0.8667	High Similarity	NPC214570
0.8667	High Similarity	NPC155986
0.8667	High Similarity	NPC198968
0.8667	High Similarity	NPC318495
0.8649	High Similarity	NPC304309
0.8649	High Similarity	NPC138374
0.8649	High Similarity	NPC141071
0.8649	High Similarity	NPC285893
0.8649	High Similarity	NPC288035
0.8649	High Similarity	NPC134847
0.8649	High Similarity	NPC34700
0.8649	High Similarity	NPC22105
0.8649	High Similarity	NPC136188
0.8649	High Similarity	NPC471723
0.8649	High Similarity	NPC162742
0.8649	High Similarity	NPC257347
0.8649	High Similarity	NPC230301
0.8649	High Similarity	NPC28657
0.8608	High Similarity	NPC238992
0.8608	High Similarity	NPC124172
0.859	High Similarity	NPC248886
0.859	High Similarity	NPC49964
0.8571	High Similarity	NPC102253
0.8571	High Similarity	NPC236237
0.8571	High Similarity	NPC222366
0.8571	High Similarity	NPC164840
0.8571	High Similarity	NPC234193
0.8571	High Similarity	NPC236112
0.8571	High Similarity	NPC241290
0.8571	High Similarity	NPC286669
0.8571	High Similarity	NPC209944
0.8571	High Similarity	NPC322313
0.8571	High Similarity	NPC295131
0.8571	High Similarity	NPC476039
0.8553	High Similarity	NPC307965
0.8553	High Similarity	NPC473943
0.8553	High Similarity	NPC18603
0.8553	High Similarity	NPC477522
0.8553	High Similarity	NPC11908
0.8553	High Similarity	NPC285761
0.8553	High Similarity	NPC76931
0.8553	High Similarity	NPC474216
0.8553	High Similarity	NPC87604
0.8553	High Similarity	NPC148977
0.8553	High Similarity	NPC72507
0.8551	High Similarity	NPC225415
0.8551	High Similarity	NPC144650
0.8551	High Similarity	NPC290367
0.8533	High Similarity	NPC96319
0.8533	High Similarity	NPC237460
0.8533	High Similarity	NPC202642
0.8533	High Similarity	NPC470749
0.8533	High Similarity	NPC73875
0.8533	High Similarity	NPC470362
0.8533	High Similarity	NPC46160
0.8514	High Similarity	NPC469534
0.8514	High Similarity	NPC476366
0.8514	High Similarity	NPC201048
0.8514	High Similarity	NPC306727
0.8514	High Similarity	NPC469593
0.8514	High Similarity	NPC469533
0.8481	Intermediate Similarity	NPC477818
0.8481	Intermediate Similarity	NPC52108
0.8481	Intermediate Similarity	NPC474789
0.8481	Intermediate Similarity	NPC253402
0.8481	Intermediate Similarity	NPC159168
0.8472	Intermediate Similarity	NPC210323
0.8472	Intermediate Similarity	NPC9942
0.8462	Intermediate Similarity	NPC470383
0.8462	Intermediate Similarity	NPC264245
0.8462	Intermediate Similarity	NPC242350
0.8462	Intermediate Similarity	NPC47761
0.8462	Intermediate Similarity	NPC116202
0.8442	Intermediate Similarity	NPC109546
0.8442	Intermediate Similarity	NPC84694
0.8442	Intermediate Similarity	NPC30986
0.8442	Intermediate Similarity	NPC209430
0.8442	Intermediate Similarity	NPC81306
0.8442	Intermediate Similarity	NPC328714
0.8442	Intermediate Similarity	NPC143182
0.8442	Intermediate Similarity	NPC28862
0.8442	Intermediate Similarity	NPC47982
0.8442	Intermediate Similarity	NPC470429
0.8429	Intermediate Similarity	NPC208198
0.8429	Intermediate Similarity	NPC60837
0.8429	Intermediate Similarity	NPC11555
0.8429	Intermediate Similarity	NPC172613
0.8429	Intermediate Similarity	NPC2728
0.8429	Intermediate Similarity	NPC282619
0.8421	Intermediate Similarity	NPC34019
0.84	Intermediate Similarity	NPC322353
0.84	Intermediate Similarity	NPC121744
0.84	Intermediate Similarity	NPC118508
0.8395	Intermediate Similarity	NPC237344
0.8395	Intermediate Similarity	NPC261266
0.8395	Intermediate Similarity	NPC24277
0.8378	Intermediate Similarity	NPC474140
0.8375	Intermediate Similarity	NPC319238
0.8375	Intermediate Similarity	NPC470077
0.8375	Intermediate Similarity	NPC205845
0.8375	Intermediate Similarity	NPC475798
0.8375	Intermediate Similarity	NPC474493
0.8375	Intermediate Similarity	NPC478102
0.8375	Intermediate Similarity	NPC127606
0.8375	Intermediate Similarity	NPC209802
0.8356	Intermediate Similarity	NPC34834
0.8354	Intermediate Similarity	NPC470049
0.8354	Intermediate Similarity	NPC304285
0.8354	Intermediate Similarity	NPC470614
0.8354	Intermediate Similarity	NPC1272
0.8354	Intermediate Similarity	NPC87489
0.8354	Intermediate Similarity	NPC296701
0.8354	Intermediate Similarity	NPC101462
0.8354	Intermediate Similarity	NPC47763
0.8354	Intermediate Similarity	NPC30166
0.8354	Intermediate Similarity	NPC50964

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 NPC291503 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	1602
0.2-0.3	4093
0.3-0.4	2289
0.4-0.5	595
0.5-0.6	209
0.6-0.7	144
0.7-0.8	50
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8684	High Similarity	NPD7645	Phase 2
0.8649	High Similarity	NPD7339	Approved
0.8649	High Similarity	NPD6942	Approved
0.8571	High Similarity	NPD7525	Registered
0.8533	High Similarity	NPD3701	Clinical (unspecified phase)
0.8158	Intermediate Similarity	NPD8264	Approved
0.8026	Intermediate Similarity	NPD6924	Approved
0.8026	Intermediate Similarity	NPD6926	Approved
0.8	Intermediate Similarity	NPD7152	Approved
0.8	Intermediate Similarity	NPD7150	Approved
0.8	Intermediate Similarity	NPD7151	Approved
0.7927	Intermediate Similarity	NPD4786	Approved
0.7901	Intermediate Similarity	NPD3667	Approved
0.7875	Intermediate Similarity	NPD7509	Discontinued
0.7867	Intermediate Similarity	NPD7144	Approved
0.7867	Intermediate Similarity	NPD7143	Approved
0.7821	Intermediate Similarity	NPD6933	Approved
0.7792	Intermediate Similarity	NPD4785	Approved
0.7792	Intermediate Similarity	NPD4784	Approved
0.7738	Intermediate Similarity	NPD3618	Phase 1
0.7733	Intermediate Similarity	NPD6922	Approved
0.7733	Intermediate Similarity	NPD6923	Approved
0.7701	Intermediate Similarity	NPD6079	Approved
0.7674	Intermediate Similarity	NPD5328	Approved
0.7532	Intermediate Similarity	NPD4243	Approved
0.7531	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD7515	Phase 2
0.75	Intermediate Similarity	NPD6932	Approved
0.7442	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6930	Phase 2
0.7439	Intermediate Similarity	NPD6931	Approved
0.7439	Intermediate Similarity	NPD4748	Discontinued
0.7416	Intermediate Similarity	NPD4202	Approved
0.7407	Intermediate Similarity	NPD7145	Approved
0.7407	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3133	Approved
0.7294	Intermediate Similarity	NPD3666	Approved
0.7294	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD3665	Phase 1
0.7284	Intermediate Similarity	NPD6925	Approved
0.7284	Intermediate Similarity	NPD5776	Phase 2
0.7229	Intermediate Similarity	NPD7332	Phase 2
0.7229	Intermediate Similarity	NPD7514	Phase 3
0.7222	Intermediate Similarity	NPD6399	Phase 3
0.7176	Intermediate Similarity	NPD6695	Phase 3
0.7174	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD5221	Approved
0.7174	Intermediate Similarity	NPD5222	Approved
0.7143	Intermediate Similarity	NPD6902	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7128	Intermediate Similarity	NPD5286	Approved
0.7128	Intermediate Similarity	NPD4696	Approved
0.7128	Intermediate Similarity	NPD5285	Approved
0.7108	Intermediate Similarity	NPD6683	Phase 2
0.7108	Intermediate Similarity	NPD4195	Approved
0.7097	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD7902	Approved
0.7097	Intermediate Similarity	NPD5173	Approved
0.7093	Intermediate Similarity	NPD3668	Phase 3
0.7053	Intermediate Similarity	NPD5223	Approved
0.7037	Intermediate Similarity	NPD4190	Phase 3
0.7037	Intermediate Similarity	NPD5275	Approved
0.7027	Intermediate Similarity	NPD368	Approved
0.7024	Intermediate Similarity	NPD4695	Discontinued
0.7021	Intermediate Similarity	NPD5290	Discontinued
0.7011	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD6893	Approved
0.6989	Remote Similarity	NPD4697	Phase 3
0.6979	Remote Similarity	NPD4633	Approved
0.6979	Remote Similarity	NPD5224	Approved
0.6979	Remote Similarity	NPD5225	Approved
0.6979	Remote Similarity	NPD5226	Approved
0.6979	Remote Similarity	NPD5211	Phase 2
0.6947	Remote Similarity	NPD4700	Approved
0.6941	Remote Similarity	NPD6898	Phase 1
0.6932	Remote Similarity	NPD5279	Phase 3
0.6923	Remote Similarity	NPD6411	Approved
0.6907	Remote Similarity	NPD5174	Approved
0.6907	Remote Similarity	NPD5175	Approved
0.6854	Remote Similarity	NPD7750	Discontinued
0.6854	Remote Similarity	NPD7524	Approved
0.6842	Remote Similarity	NPD7638	Approved
0.6837	Remote Similarity	NPD5141	Approved
0.6824	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6881	Approved
0.68	Remote Similarity	NPD6899	Approved
0.6774	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7900	Approved
0.6771	Remote Similarity	NPD7639	Approved
0.6771	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD6402	Approved
0.6768	Remote Similarity	NPD7128	Approved
0.6768	Remote Similarity	NPD5739	Approved
0.6768	Remote Similarity	NPD6675	Approved
0.6735	Remote Similarity	NPD4754	Approved
0.6703	Remote Similarity	NPD4753	Phase 2
0.6703	Remote Similarity	NPD6101	Approved
0.6703	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.67	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD4223	Phase 3
0.6667	Remote Similarity	NPD4221	Approved
0.6667	Remote Similarity	NPD4225	Approved
0.6634	Remote Similarity	NPD7320	Approved
0.6634	Remote Similarity	NPD6011	Approved
0.6634	Remote Similarity	NPD4729	Approved
0.6634	Remote Similarity	NPD4730	Approved
0.6629	Remote Similarity	NPD5329	Approved
0.6625	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD6847	Approved
0.6602	Remote Similarity	NPD8130	Phase 1
0.6602	Remote Similarity	NPD6649	Approved
0.6602	Remote Similarity	NPD6650	Approved
0.6602	Remote Similarity	NPD6617	Approved
0.6602	Remote Similarity	NPD6869	Approved
0.66	Remote Similarity	NPD4768	Approved
0.66	Remote Similarity	NPD4767	Approved
0.6569	Remote Similarity	NPD6372	Approved
0.6569	Remote Similarity	NPD6012	Approved
0.6569	Remote Similarity	NPD6014	Approved
0.6569	Remote Similarity	NPD6013	Approved
0.6569	Remote Similarity	NPD6373	Approved
0.6559	Remote Similarity	NPD8035	Phase 2
0.6559	Remote Similarity	NPD8034	Phase 2
0.6559	Remote Similarity	NPD7087	Discontinued
0.6556	Remote Similarity	NPD6409	Approved
0.6556	Remote Similarity	NPD7146	Approved
0.6556	Remote Similarity	NPD5330	Approved
0.6556	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4519	Discontinued
0.6556	Remote Similarity	NPD7521	Approved
0.6556	Remote Similarity	NPD7334	Approved
0.6556	Remote Similarity	NPD4623	Approved
0.6556	Remote Similarity	NPD6684	Approved
0.6538	Remote Similarity	NPD6882	Approved
0.6538	Remote Similarity	NPD8297	Approved
0.6535	Remote Similarity	NPD5701	Approved
0.6526	Remote Similarity	NPD4629	Approved
0.6526	Remote Similarity	NPD5210	Approved
0.6517	Remote Similarity	NPD4197	Approved
0.6505	Remote Similarity	NPD5249	Phase 3
0.6505	Remote Similarity	NPD5169	Approved
0.6505	Remote Similarity	NPD5248	Approved
0.6505	Remote Similarity	NPD5250	Approved
0.6505	Remote Similarity	NPD5251	Approved
0.6505	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD5247	Approved
0.6505	Remote Similarity	NPD5135	Approved
0.6505	Remote Similarity	NPD4634	Approved
0.6484	Remote Similarity	NPD3573	Approved
0.6471	Remote Similarity	NPD5168	Approved
0.6471	Remote Similarity	NPD5128	Approved
0.6452	Remote Similarity	NPD7136	Phase 2
0.6442	Remote Similarity	NPD5216	Approved
0.6442	Remote Similarity	NPD5217	Approved
0.6442	Remote Similarity	NPD5215	Approved
0.6442	Remote Similarity	NPD5127	Approved
0.6442	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD342	Phase 1
0.6413	Remote Similarity	NPD6903	Approved
0.6413	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD4788	Approved
0.6395	Remote Similarity	NPD3617	Approved
0.6392	Remote Similarity	NPD6083	Phase 2
0.6392	Remote Similarity	NPD6084	Phase 2
0.6383	Remote Similarity	NPD7637	Suspended
0.6374	Remote Similarity	NPD5690	Phase 2
0.6374	Remote Similarity	NPD4690	Approved
0.6374	Remote Similarity	NPD5205	Approved
0.6374	Remote Similarity	NPD4138	Approved
0.6374	Remote Similarity	NPD4689	Approved
0.6374	Remote Similarity	NPD4688	Approved
0.6374	Remote Similarity	NPD4693	Phase 3
0.6364	Remote Similarity	NPD4159	Approved
0.6351	Remote Similarity	NPD4219	Approved
0.6344	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6344	Remote Similarity	NPD6051	Approved
0.6341	Remote Similarity	NPD4787	Phase 1
0.6321	Remote Similarity	NPD4632	Approved
0.6316	Remote Similarity	NPD5778	Approved
0.6316	Remote Similarity	NPD5779	Approved
0.6296	Remote Similarity	NPD7115	Discovery
0.6279	Remote Similarity	NPD6116	Phase 1
0.6265	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6265	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD5167	Approved
0.6239	Remote Similarity	NPD6335	Approved
0.6237	Remote Similarity	NPD6672	Approved
0.6237	Remote Similarity	NPD4723	Approved
0.6237	Remote Similarity	NPD4722	Approved
0.6237	Remote Similarity	NPD5737	Approved
0.622	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.622	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD6412	Phase 2
0.6211	Remote Similarity	NPD5284	Approved
0.6211	Remote Similarity	NPD5281	Approved
0.6204	Remote Similarity	NPD6868	Approved
0.62	Remote Similarity	NPD5344	Discontinued

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