NPASS Compound

Structure

NPC287749 OpenBabel07101719242D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.8228 -2.7247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3914 -0.8912 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 -2.8569 -2.4659 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 -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 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 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 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 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 0.8660 -0.5000 0.0000 C 0 0 1 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 -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 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 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 12 1 0 0 0 0 8 15 1 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 14 1 0 0 0 0 10 18 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 13 16 1 0 0 0 0 13 21 1 6 0 0 0 14 17 1 0 0 0 0 14 22 1 6 0 0 0 15 18 1 0 0 0 0 15 20 1 1 0 0 0 16 20 1 1 0 0 0 17 20 1 6 0 0 0 17 23 1 0 0 0 0 19 4 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	3.137
LogD:	2.713
LogS:	-3.844
# Rotatable Bonds:	1
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.651
Synthetic Accessibility Score:	5.136
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:	-4.799
MDCK Permeability:	1.8526368876337074e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.811
Human Intestinal Absorption (HIA):	0.027
20% Bioavailability (F20%):	0.071
30% Bioavailability (F30%):	0.011

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.664
Plasma Protein Binding (PPB):	85.37577056884766%
Volume Distribution (VD):	1.721
Pgp-substrate:	19.538223266601562%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.258
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.779
CYP2C9-inhibitor:	0.033
CYP2C9-substrate:	0.309
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.596
CYP3A4-substrate:	0.264

ADMET: Excretion

Clearance (CL):	2.656
Half-life (T1/2):	0.493

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.155
Drug-inuced Liver Injury (DILI):	0.043
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.794
Maximum Recommended Daily Dose:	0.75
Skin Sensitization:	0.117
Carcinogencity:	0.576
Eye Corrosion:	0.054
Eye Irritation:	0.039
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC287749

Natural Product ID:	NPC287749
*Common Name:**	(1R,2S,5S,9S,10S,11R,13R)-1,2,11-Trihydroxypimara-8(14),15-Diene
IUPAC Name:	(3S,4R,4aS,4bS,5R,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-3,4,4b,5,6,9,10,10a-octahydro-2H-phenanthrene-3,4,5-triol
Synonyms:
Standard InCHIKey:	JEXXIARQVKWIJS-ILNMQHDMSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-6-19(4)9-12-7-8-15-18(2,3)10-14(22)17(23)20(15,5)16(12)13(21)11-19/h6,9,13-17,21-23H,1,7-8,10-11H2,2-5H3/t13-,14+,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)[C@@H](O)CC1(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL503726
PubChem CID:	11522629
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
MIC	1
Others	8

Activity Type	# Activity
Cell Line	9
Organism	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	17.25	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	11.11	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	37.12	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	22.37	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	65.71	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	50.85	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	60.89	%	PMID[550242]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	66.53	%	PMID[550242]
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	8.8	ug.mL-1	PMID[550240]
NPT88	Organism	Mycobacterium tuberculosis	Mycobacterium tuberculosis	MIC	>	100.0	ug.mL-1	PMID[550240]
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	17.5	ug.mL-1	PMID[550240]

☑ 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 NPC287749 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	191
0.1-0.2	1430
0.2-0.3	5198
0.3-0.4	13970
0.4-0.5	10591
0.5-0.6	5870
0.6-0.7	4164
0.7-0.8	1091
0.8-0.85	128
0.85-0.9	32
0.9-0.95	30
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9333	High Similarity	NPC130136
0.9333	High Similarity	NPC471798
0.9324	High Similarity	NPC477923
0.9324	High Similarity	NPC66566
0.9324	High Similarity	NPC291503
0.9221	High Similarity	NPC96362
0.92	High Similarity	NPC274079
0.92	High Similarity	NPC477925
0.9189	High Similarity	NPC243342
0.9189	High Similarity	NPC477138
0.9103	High Similarity	NPC476646
0.9079	High Similarity	NPC477924
0.9012	High Similarity	NPC237344
0.8933	High Similarity	NPC91858
0.8919	High Similarity	NPC242001
0.8861	High Similarity	NPC474531
0.88	High Similarity	NPC182717
0.88	High Similarity	NPC471799
0.8795	High Similarity	NPC133588
0.8784	High Similarity	NPC145498
0.878	High Similarity	NPC94462
0.8765	High Similarity	NPC238992
0.8734	High Similarity	NPC236112
0.8718	High Similarity	NPC83351
0.8718	High Similarity	NPC167891
0.8701	High Similarity	NPC253190
0.8701	High Similarity	NPC106432
0.869	High Similarity	NPC105495
0.8684	High Similarity	NPC471797
0.8642	High Similarity	NPC159168
0.8642	High Similarity	NPC253402
0.8625	High Similarity	NPC249423
0.8608	High Similarity	NPC472463
0.859	High Similarity	NPC91594
0.8588	High Similarity	NPC291484
0.8588	High Similarity	NPC3345
0.8588	High Similarity	NPC11216
0.8588	High Similarity	NPC329596
0.8588	High Similarity	NPC80561
0.8588	High Similarity	NPC204188
0.8571	High Similarity	NPC474668
0.8571	High Similarity	NPC475664
0.8553	High Similarity	NPC95165
0.8553	High Similarity	NPC68443
0.8537	High Similarity	NPC124172
0.8533	High Similarity	NPC92801
0.8519	High Similarity	NPC248886
0.8519	High Similarity	NPC47763
0.8488	Intermediate Similarity	NPC41554
0.8488	Intermediate Similarity	NPC97404
0.8481	Intermediate Similarity	NPC87604
0.8481	Intermediate Similarity	NPC470396
0.8481	Intermediate Similarity	NPC474989
0.8481	Intermediate Similarity	NPC300499
0.8481	Intermediate Similarity	NPC148977
0.8481	Intermediate Similarity	NPC99168
0.8481	Intermediate Similarity	NPC22955
0.8471	Intermediate Similarity	NPC187785
0.8471	Intermediate Similarity	NPC470361
0.8471	Intermediate Similarity	NPC259875
0.8462	Intermediate Similarity	NPC265588
0.8452	Intermediate Similarity	NPC474657
0.8452	Intermediate Similarity	NPC186145
0.8452	Intermediate Similarity	NPC189777
0.8442	Intermediate Similarity	NPC306727
0.8442	Intermediate Similarity	NPC100334
0.8434	Intermediate Similarity	NPC290731
0.8421	Intermediate Similarity	NPC167706
0.8421	Intermediate Similarity	NPC110799
0.8421	Intermediate Similarity	NPC242992
0.8415	Intermediate Similarity	NPC207013
0.8415	Intermediate Similarity	NPC317458
0.8415	Intermediate Similarity	NPC477818
0.8395	Intermediate Similarity	NPC470383
0.8395	Intermediate Similarity	NPC142163
0.8395	Intermediate Similarity	NPC242350
0.8375	Intermediate Similarity	NPC291379
0.8375	Intermediate Similarity	NPC53744
0.8375	Intermediate Similarity	NPC328714
0.8372	Intermediate Similarity	NPC475751
0.8372	Intermediate Similarity	NPC473956
0.8354	Intermediate Similarity	NPC90979
0.8354	Intermediate Similarity	NPC157996
0.8354	Intermediate Similarity	NPC40394
0.8354	Intermediate Similarity	NPC34177
0.8354	Intermediate Similarity	NPC472805
0.8354	Intermediate Similarity	NPC101475
0.8333	Intermediate Similarity	NPC261266
0.8333	Intermediate Similarity	NPC71520
0.8333	Intermediate Similarity	NPC24277
0.8333	Intermediate Similarity	NPC269058
0.8315	Intermediate Similarity	NPC210717
0.8315	Intermediate Similarity	NPC103165
0.8313	Intermediate Similarity	NPC474493
0.8313	Intermediate Similarity	NPC475798
0.8313	Intermediate Similarity	NPC127606
0.8313	Intermediate Similarity	NPC209802
0.8295	Intermediate Similarity	NPC65402
0.8295	Intermediate Similarity	NPC127718
0.8293	Intermediate Similarity	NPC470614
0.8293	Intermediate Similarity	NPC1272
0.8293	Intermediate Similarity	NPC50964
0.8293	Intermediate Similarity	NPC30166
0.8293	Intermediate Similarity	NPC7988
0.8272	Intermediate Similarity	NPC13554
0.8272	Intermediate Similarity	NPC26117
0.8267	Intermediate Similarity	NPC208999
0.8256	Intermediate Similarity	NPC97103
0.8256	Intermediate Similarity	NPC109744
0.8256	Intermediate Similarity	NPC115607
0.825	Intermediate Similarity	NPC230295
0.825	Intermediate Similarity	NPC138621
0.825	Intermediate Similarity	NPC476314
0.825	Intermediate Similarity	NPC196753
0.825	Intermediate Similarity	NPC6978
0.825	Intermediate Similarity	NPC275910
0.825	Intermediate Similarity	NPC253807
0.825	Intermediate Similarity	NPC167037
0.825	Intermediate Similarity	NPC244385
0.825	Intermediate Similarity	NPC98386
0.825	Intermediate Similarity	NPC158662
0.8235	Intermediate Similarity	NPC470620
0.8228	Intermediate Similarity	NPC134330
0.8228	Intermediate Similarity	NPC189883
0.8228	Intermediate Similarity	NPC30590
0.8228	Intermediate Similarity	NPC107059
0.8228	Intermediate Similarity	NPC290598
0.8228	Intermediate Similarity	NPC300324
0.8228	Intermediate Similarity	NPC265328
0.8228	Intermediate Similarity	NPC122418
0.8228	Intermediate Similarity	NPC63958
0.8228	Intermediate Similarity	NPC106364
0.8228	Intermediate Similarity	NPC240604
0.8228	Intermediate Similarity	NPC113733
0.8228	Intermediate Similarity	NPC321381
0.8228	Intermediate Similarity	NPC321016
0.8228	Intermediate Similarity	NPC129165
0.8228	Intermediate Similarity	NPC120098
0.8228	Intermediate Similarity	NPC27765
0.8202	Intermediate Similarity	NPC8774
0.8193	Intermediate Similarity	NPC110778
0.8193	Intermediate Similarity	NPC82538
0.8193	Intermediate Similarity	NPC237795
0.8193	Intermediate Similarity	NPC141941
0.8193	Intermediate Similarity	NPC193870
0.8182	Intermediate Similarity	NPC471268
0.8182	Intermediate Similarity	NPC164022
0.8182	Intermediate Similarity	NPC310013
0.8182	Intermediate Similarity	NPC471271
0.8182	Intermediate Similarity	NPC119379
0.8171	Intermediate Similarity	NPC471270
0.8171	Intermediate Similarity	NPC23852
0.8171	Intermediate Similarity	NPC209620
0.8148	Intermediate Similarity	NPC100906
0.8148	Intermediate Similarity	NPC80530
0.8148	Intermediate Similarity	NPC1319
0.8148	Intermediate Similarity	NPC273410
0.814	Intermediate Similarity	NPC470542
0.8133	Intermediate Similarity	NPC197805
0.8125	Intermediate Similarity	NPC155986
0.8125	Intermediate Similarity	NPC470711
0.8125	Intermediate Similarity	NPC198968
0.8125	Intermediate Similarity	NPC214570
0.8125	Intermediate Similarity	NPC470758
0.8125	Intermediate Similarity	NPC318495
0.8118	Intermediate Similarity	NPC476217
0.8118	Intermediate Similarity	NPC6391
0.8118	Intermediate Similarity	NPC477604
0.8118	Intermediate Similarity	NPC299068
0.8111	Intermediate Similarity	NPC288970
0.8111	Intermediate Similarity	NPC98457
0.8111	Intermediate Similarity	NPC227583
0.8111	Intermediate Similarity	NPC12103
0.8101	Intermediate Similarity	NPC288035
0.8101	Intermediate Similarity	NPC28657
0.8101	Intermediate Similarity	NPC32832
0.8101	Intermediate Similarity	NPC304309
0.8101	Intermediate Similarity	NPC162742
0.8101	Intermediate Similarity	NPC134847
0.8101	Intermediate Similarity	NPC34700
0.8101	Intermediate Similarity	NPC22105
0.8101	Intermediate Similarity	NPC257347
0.8101	Intermediate Similarity	NPC141071
0.8101	Intermediate Similarity	NPC230301
0.8101	Intermediate Similarity	NPC471723
0.8101	Intermediate Similarity	NPC138374
0.8101	Intermediate Similarity	NPC285893
0.8101	Intermediate Similarity	NPC136188
0.8095	Intermediate Similarity	NPC255882
0.8095	Intermediate Similarity	NPC185568
0.8095	Intermediate Similarity	NPC319238
0.809	Intermediate Similarity	NPC477927
0.809	Intermediate Similarity	NPC305160
0.809	Intermediate Similarity	NPC72817
0.8072	Intermediate Similarity	NPC49964
0.8068	Intermediate Similarity	NPC210268
0.8049	Intermediate Similarity	NPC236707
0.8049	Intermediate Similarity	NPC209944
0.8049	Intermediate Similarity	NPC322313
0.8049	Intermediate Similarity	NPC236237

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 NPC287749 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1699
0.2-0.3	4033
0.3-0.4	2201
0.4-0.5	653
0.5-0.6	200
0.6-0.7	145
0.7-0.8	38
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
0.8148	Intermediate Similarity	NPD7645	Phase 2
0.8101	Intermediate Similarity	NPD6942	Approved
0.8101	Intermediate Similarity	NPD7339	Approved
0.8049	Intermediate Similarity	NPD7525	Registered
0.8	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD6933	Approved
0.7654	Intermediate Similarity	NPD8264	Approved
0.7531	Intermediate Similarity	NPD6924	Approved
0.7531	Intermediate Similarity	NPD6926	Approved
0.75	Intermediate Similarity	NPD7152	Approved
0.75	Intermediate Similarity	NPD6929	Approved
0.75	Intermediate Similarity	NPD7151	Approved
0.75	Intermediate Similarity	NPD7150	Approved
0.7471	Intermediate Similarity	NPD4786	Approved
0.747	Intermediate Similarity	NPD6932	Approved
0.7442	Intermediate Similarity	NPD3667	Approved
0.7416	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD7524	Approved
0.7412	Intermediate Similarity	NPD7509	Discontinued
0.7412	Intermediate Similarity	NPD6931	Approved
0.7412	Intermediate Similarity	NPD6930	Phase 2
0.7381	Intermediate Similarity	NPD7145	Approved
0.7375	Intermediate Similarity	NPD7143	Approved
0.7375	Intermediate Similarity	NPD7144	Approved
0.7317	Intermediate Similarity	NPD4784	Approved
0.7317	Intermediate Similarity	NPD4785	Approved
0.7303	Intermediate Similarity	NPD3618	Phase 1
0.7283	Intermediate Similarity	NPD6079	Approved
0.7273	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD5776	Phase 2
0.7262	Intermediate Similarity	NPD6925	Approved
0.7253	Intermediate Similarity	NPD5328	Approved
0.725	Intermediate Similarity	NPD6923	Approved
0.725	Intermediate Similarity	NPD6922	Approved
0.7209	Intermediate Similarity	NPD7514	Phase 3
0.7209	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD6695	Phase 3
0.7126	Intermediate Similarity	NPD6902	Approved
0.7097	Intermediate Similarity	NPD7515	Phase 2
0.7093	Intermediate Similarity	NPD6683	Phase 2
0.7073	Intermediate Similarity	NPD4243	Approved
0.7021	Intermediate Similarity	NPD4202	Approved
0.7011	Intermediate Similarity	NPD4748	Discontinued
0.7	Intermediate Similarity	NPD6893	Approved
0.6977	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6898	Phase 1
0.6889	Remote Similarity	NPD3665	Phase 1
0.6889	Remote Similarity	NPD3666	Approved
0.6889	Remote Similarity	NPD3133	Approved
0.6848	Remote Similarity	NPD7750	Discontinued
0.6842	Remote Similarity	NPD6399	Phase 3
0.6837	Remote Similarity	NPD7638	Approved
0.6827	Remote Similarity	NPD4634	Approved
0.6804	Remote Similarity	NPD5222	Approved
0.6804	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5221	Approved
0.6771	Remote Similarity	NPD7748	Approved
0.6768	Remote Similarity	NPD7640	Approved
0.6768	Remote Similarity	NPD5286	Approved
0.6768	Remote Similarity	NPD7639	Approved
0.6768	Remote Similarity	NPD5285	Approved
0.6768	Remote Similarity	NPD4696	Approved
0.6735	Remote Similarity	NPD5173	Approved
0.6735	Remote Similarity	NPD4755	Approved
0.6735	Remote Similarity	NPD7902	Approved
0.6705	Remote Similarity	NPD4195	Approved
0.6703	Remote Similarity	NPD3668	Phase 3
0.67	Remote Similarity	NPD5223	Approved
0.67	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD4225	Approved
0.6667	Remote Similarity	NPD5290	Discontinued
0.6636	Remote Similarity	NPD4632	Approved
0.6634	Remote Similarity	NPD5226	Approved
0.6634	Remote Similarity	NPD5224	Approved
0.6634	Remote Similarity	NPD5225	Approved
0.6634	Remote Similarity	NPD4633	Approved
0.6634	Remote Similarity	NPD5211	Phase 2
0.6633	Remote Similarity	NPD4697	Phase 3
0.663	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD4695	Discontinued
0.6628	Remote Similarity	NPD4190	Phase 3
0.6628	Remote Similarity	NPD5275	Approved
0.6627	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.66	Remote Similarity	NPD4700	Approved
0.6582	Remote Similarity	NPD368	Approved
0.6571	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD5174	Approved
0.6569	Remote Similarity	NPD5175	Approved
0.6562	Remote Similarity	NPD6411	Approved
0.6562	Remote Similarity	NPD7087	Discontinued
0.6559	Remote Similarity	NPD5279	Phase 3
0.6538	Remote Similarity	NPD6412	Phase 2
0.6535	Remote Similarity	NPD4159	Approved
0.6505	Remote Similarity	NPD5141	Approved
0.6476	Remote Similarity	NPD6899	Approved
0.6476	Remote Similarity	NPD6881	Approved
0.6458	Remote Similarity	NPD7136	Phase 2
0.6458	Remote Similarity	NPD3168	Discontinued
0.6444	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6675	Approved
0.6442	Remote Similarity	NPD6402	Approved
0.6442	Remote Similarity	NPD7128	Approved
0.6442	Remote Similarity	NPD5739	Approved
0.6429	Remote Similarity	NPD7900	Approved
0.6429	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4754	Approved
0.6392	Remote Similarity	NPD7637	Suspended
0.6389	Remote Similarity	NPD8297	Approved
0.6381	Remote Similarity	NPD5697	Approved
0.6355	Remote Similarity	NPD7290	Approved
0.6355	Remote Similarity	NPD6883	Approved
0.6355	Remote Similarity	NPD7102	Approved
0.6354	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6354	Remote Similarity	NPD4753	Phase 2
0.6354	Remote Similarity	NPD6101	Approved
0.6339	Remote Similarity	NPD7516	Approved
0.6327	Remote Similarity	NPD5778	Approved
0.6327	Remote Similarity	NPD5779	Approved
0.6321	Remote Similarity	NPD6686	Approved
0.6321	Remote Similarity	NPD4730	Approved
0.6321	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD4729	Approved
0.6321	Remote Similarity	NPD7320	Approved
0.6321	Remote Similarity	NPD6011	Approved
0.6306	Remote Similarity	NPD6009	Approved
0.6306	Remote Similarity	NPD7115	Discovery
0.6304	Remote Similarity	NPD4221	Approved
0.6304	Remote Similarity	NPD4223	Phase 3
0.6296	Remote Similarity	NPD6847	Approved
0.6296	Remote Similarity	NPD6869	Approved
0.6296	Remote Similarity	NPD6617	Approved
0.6296	Remote Similarity	NPD6650	Approved
0.6296	Remote Similarity	NPD6649	Approved
0.6296	Remote Similarity	NPD8130	Phase 1
0.6286	Remote Similarity	NPD4768	Approved
0.6286	Remote Similarity	NPD4767	Approved
0.6283	Remote Similarity	NPD6054	Approved
0.6283	Remote Similarity	NPD6319	Approved
0.6277	Remote Similarity	NPD5329	Approved
0.6275	Remote Similarity	NPD6648	Approved
0.6262	Remote Similarity	NPD6013	Approved
0.6262	Remote Similarity	NPD6372	Approved
0.6262	Remote Similarity	NPD6012	Approved
0.6262	Remote Similarity	NPD6014	Approved
0.6262	Remote Similarity	NPD6373	Approved
0.625	Remote Similarity	NPD7328	Approved
0.625	Remote Similarity	NPD7327	Approved
0.6239	Remote Similarity	NPD6882	Approved
0.6228	Remote Similarity	NPD7503	Approved
0.6228	Remote Similarity	NPD8033	Approved
0.6226	Remote Similarity	NPD5701	Approved
0.6224	Remote Similarity	NPD8035	Phase 2
0.6224	Remote Similarity	NPD8034	Phase 2
0.622	Remote Similarity	NPD371	Approved
0.6211	Remote Similarity	NPD7334	Approved
0.6211	Remote Similarity	NPD4623	Approved
0.6211	Remote Similarity	NPD5330	Approved
0.6211	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD6409	Approved
0.6211	Remote Similarity	NPD7146	Approved
0.6211	Remote Similarity	NPD6684	Approved
0.6211	Remote Similarity	NPD7521	Approved
0.6211	Remote Similarity	NPD4519	Discontinued
0.6207	Remote Similarity	NPD4732	Discontinued
0.6204	Remote Similarity	NPD5251	Approved
0.6204	Remote Similarity	NPD5250	Approved
0.6204	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD5135	Approved
0.6204	Remote Similarity	NPD5247	Approved
0.6204	Remote Similarity	NPD5249	Phase 3
0.6204	Remote Similarity	NPD5169	Approved
0.6204	Remote Similarity	NPD5248	Approved
0.62	Remote Similarity	NPD4629	Approved
0.62	Remote Similarity	NPD5210	Approved
0.6174	Remote Similarity	NPD6370	Approved
0.617	Remote Similarity	NPD4197	Approved
0.6168	Remote Similarity	NPD5168	Approved
0.6168	Remote Similarity	NPD5128	Approved
0.6161	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7632	Discontinued
0.6147	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5215	Approved
0.6147	Remote Similarity	NPD5127	Approved
0.6147	Remote Similarity	NPD5217	Approved
0.6147	Remote Similarity	NPD5216	Approved
0.6146	Remote Similarity	NPD3573	Approved
0.614	Remote Similarity	NPD6059	Approved
0.614	Remote Similarity	NPD8294	Approved
0.614	Remote Similarity	NPD8377	Approved
0.6132	Remote Similarity	NPD6008	Approved
0.6121	Remote Similarity	NPD7604	Phase 2
0.6121	Remote Similarity	NPD8328	Phase 3
0.6087	Remote Similarity	NPD6016	Approved
0.6087	Remote Similarity	NPD8335	Approved
0.6087	Remote Similarity	NPD6015	Approved
0.6087	Remote Similarity	NPD8378	Approved
0.6087	Remote Similarity	NPD8379	Approved
0.6087	Remote Similarity	NPD8380	Approved
0.6087	Remote Similarity	NPD8296	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