NPASS Compound

Structure

NPC249423 OpenBabel07101718322D 22 24 0 0 1 0 0 0 0 0999 V2000 2.8385 2.1358 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9742 0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4542 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4244 0.3756 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9112 1.8873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -1.9200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.4400 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6628 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4942 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.9600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8314 -0.4800 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 -0.8314 2.4000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 5 19 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 9 1 0 0 0 0 8 17 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 18 1 0 0 0 0 11 20 1 0 0 0 0 12 15 1 0 0 0 0 12 16 1 0 0 0 0 13 14 2 0 0 0 0 13 18 1 0 0 0 0 14 15 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 6 0 0 0 16 17 1 0 0 0 0 16 19 1 6 0 0 0 18 4 1 6 0 0 0 19 20 1 1 0 0 0 20 22 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	304.24
Volume:	341.114
LogP:	3.8
LogD:	3.219
LogS:	-4.836
# 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:	0.712
Synthetic Accessibility Score:	4.768
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:	-4.663
MDCK Permeability:	2.5853960323729552e-05
Pgp-inhibitor:	0.944
Pgp-substrate:	0.216
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.043
30% Bioavailability (F30%):	0.006

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.935
Plasma Protein Binding (PPB):	88.64483642578125%
Volume Distribution (VD):	1.558
Pgp-substrate:	14.593108177185059%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.594
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.805
CYP2C9-inhibitor:	0.171
CYP2C9-substrate:	0.073
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.873
CYP3A4-substrate:	0.803

ADMET: Excretion

Clearance (CL):	5.568
Half-life (T1/2):	0.085

ADMET: Toxicity

hERG Blockers:	0.097
Human Hepatotoxicity (H-HT):	0.329
Drug-inuced Liver Injury (DILI):	0.027
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.954
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.146
Carcinogencity:	0.965
Eye Corrosion:	0.195
Eye Irritation:	0.454
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC249423

Natural Product ID:	NPC249423
*Common Name:**	7Beta,9Alpha-Dihydroxypimara-8(14),15-Diene
IUPAC Name:	(2R,4aS,4bS,8aS,10S)-2-ethenyl-2,4b,8,8-tetramethyl-3,4,5,6,7,8a,9,10-octahydrophenanthrene-4a,10-diol
Synonyms:
Standard InCHIKey:	ZGGQYGIKHFZLQI-CZKCSJLSSA-N
Standard InCHI:	InChI=1S/C20H32O2/c1-6-18(4)10-11-20(22)14(13-18)15(21)12-16-17(2,3)8-7-9-19(16,20)5/h6,13,15-16,21-22H,1,7-12H2,2-5H3/t15-,16-,18-,19-,20+/m0/s1
SMILES:	C=C[C@@]1(C)CC[C@]2(C(=C1)[C@H](C[C@H]1C(C)(C)CCC[C@]21C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2017494
PubChem CID:	70695903
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes and derivatives [CHEMONTID:0000223] Hydrophenanthrenes

*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
NPO33396	Epicoccum sp. HS-1	Species	Didymellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22418279]
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]
NPO22194	Kaempferia pulchra	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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	>	100.0	ug.mL-1	PMID[495497]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	18.38	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	14.81	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	5.89	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Inhibition	=	-5.96	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	>	100000.0	nM	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	113.97	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	98.8	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	73.32	%	PMID[495499]
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	71.32	%	PMID[495499]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	100.0	ug.mL-1	PMID[495497]

☑ 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 NPC249423 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	188
0.1-0.2	1400
0.2-0.3	5000
0.3-0.4	12874
0.4-0.5	11661
0.5-0.6	6228
0.6-0.7	4042
0.7-0.8	1075
0.8-0.85	161
0.85-0.9	52
0.9-0.95	14
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9351	High Similarity	NPC96362
0.9333	High Similarity	NPC253190
0.925	High Similarity	NPC470360
0.9231	High Similarity	NPC476646
0.9136	High Similarity	NPC299068
0.9067	High Similarity	NPC306727
0.9067	High Similarity	NPC91858
0.8961	High Similarity	NPC470711
0.8961	High Similarity	NPC91594
0.8961	High Similarity	NPC471798
0.8961	High Similarity	NPC470758
0.8947	High Similarity	NPC32832
0.8929	High Similarity	NPC80561
0.8929	High Similarity	NPC329596
0.8929	High Similarity	NPC204188
0.8929	High Similarity	NPC3345
0.8929	High Similarity	NPC291484
0.8929	High Similarity	NPC11216
0.8902	High Similarity	NPC6391
0.8902	High Similarity	NPC261266
0.8831	High Similarity	NPC470749
0.8831	High Similarity	NPC265588
0.8824	High Similarity	NPC97404
0.8824	High Similarity	NPC41554
0.8816	High Similarity	NPC243342
0.8816	High Similarity	NPC201048
0.8816	High Similarity	NPC476366
0.8816	High Similarity	NPC477138
0.881	High Similarity	NPC470361
0.875	High Similarity	NPC242350
0.8701	High Similarity	NPC291503
0.869	High Similarity	NPC133588
0.8684	High Similarity	NPC182717
0.8659	High Similarity	NPC205845
0.8642	High Similarity	NPC49964
0.8642	High Similarity	NPC296701
0.8642	High Similarity	NPC87489
0.8642	High Similarity	NPC50964
0.8642	High Similarity	NPC218616
0.8625	High Similarity	NPC287749
0.8625	High Similarity	NPC295131
0.8621	High Similarity	NPC144202
0.8608	High Similarity	NPC476314
0.8608	High Similarity	NPC83351
0.8608	High Similarity	NPC167891
0.8608	High Similarity	NPC11908
0.859	High Similarity	NPC63958
0.8588	High Similarity	NPC101886
0.8588	High Similarity	NPC259875
0.8588	High Similarity	NPC187785
0.8571	High Similarity	NPC471797
0.8553	High Similarity	NPC242001
0.8553	High Similarity	NPC167706
0.8533	High Similarity	NPC9942
0.8519	High Similarity	NPC23852
0.8519	High Similarity	NPC264245
0.8519	High Similarity	NPC470383
0.8519	High Similarity	NPC209620
0.8506	High Similarity	NPC27531
0.8506	High Similarity	NPC310013
0.85	High Similarity	NPC30986
0.85	High Similarity	NPC209430
0.8488	Intermediate Similarity	NPC470390
0.8488	Intermediate Similarity	NPC245410
0.8488	Intermediate Similarity	NPC270511
0.8488	Intermediate Similarity	NPC14380
0.8488	Intermediate Similarity	NPC192437
0.8488	Intermediate Similarity	NPC295668
0.8481	Intermediate Similarity	NPC130136
0.8481	Intermediate Similarity	NPC477924
0.8471	Intermediate Similarity	NPC4574
0.8471	Intermediate Similarity	NPC212596
0.8462	Intermediate Similarity	NPC477923
0.8462	Intermediate Similarity	NPC66566
0.8452	Intermediate Similarity	NPC152808
0.8452	Intermediate Similarity	NPC293287
0.8442	Intermediate Similarity	NPC471799
0.8442	Intermediate Similarity	NPC220939
0.8442	Intermediate Similarity	NPC265485
0.8434	Intermediate Similarity	NPC470077
0.8434	Intermediate Similarity	NPC231310
0.8427	Intermediate Similarity	NPC210717
0.8427	Intermediate Similarity	NPC288970
0.8427	Intermediate Similarity	NPC103165
0.8421	Intermediate Similarity	NPC145498
0.8421	Intermediate Similarity	NPC283316
0.8421	Intermediate Similarity	NPC34834
0.8415	Intermediate Similarity	NPC101462
0.8415	Intermediate Similarity	NPC155521
0.8409	Intermediate Similarity	NPC127718
0.8409	Intermediate Similarity	NPC65402
0.8395	Intermediate Similarity	NPC471266
0.8395	Intermediate Similarity	NPC241290
0.8395	Intermediate Similarity	NPC209944
0.8395	Intermediate Similarity	NPC234193
0.8395	Intermediate Similarity	NPC95124
0.8395	Intermediate Similarity	NPC164840
0.8391	Intermediate Similarity	NPC275671
0.8375	Intermediate Similarity	NPC148977
0.8375	Intermediate Similarity	NPC253807
0.8375	Intermediate Similarity	NPC230295
0.8375	Intermediate Similarity	NPC158662
0.8375	Intermediate Similarity	NPC98386
0.8375	Intermediate Similarity	NPC196753
0.8372	Intermediate Similarity	NPC138974
0.8354	Intermediate Similarity	NPC106432
0.8353	Intermediate Similarity	NPC149224
0.8353	Intermediate Similarity	NPC304083
0.8333	Intermediate Similarity	NPC469533
0.8333	Intermediate Similarity	NPC100334
0.8333	Intermediate Similarity	NPC318390
0.8333	Intermediate Similarity	NPC469534
0.8333	Intermediate Similarity	NPC469593
0.8333	Intermediate Similarity	NPC274448
0.8315	Intermediate Similarity	NPC266899
0.8315	Intermediate Similarity	NPC8774
0.8315	Intermediate Similarity	NPC272617
0.8313	Intermediate Similarity	NPC113978
0.8313	Intermediate Similarity	NPC82623
0.8312	Intermediate Similarity	NPC471272
0.8312	Intermediate Similarity	NPC110799
0.8312	Intermediate Similarity	NPC23954
0.8293	Intermediate Similarity	NPC471270
0.8293	Intermediate Similarity	NPC47761
0.8272	Intermediate Similarity	NPC472463
0.8272	Intermediate Similarity	NPC109546
0.8272	Intermediate Similarity	NPC143182
0.8272	Intermediate Similarity	NPC291379
0.8272	Intermediate Similarity	NPC28862
0.8272	Intermediate Similarity	NPC53744
0.8272	Intermediate Similarity	NPC47982
0.8272	Intermediate Similarity	NPC84694
0.8272	Intermediate Similarity	NPC81306
0.8267	Intermediate Similarity	NPC69649
0.8267	Intermediate Similarity	NPC68703
0.8256	Intermediate Similarity	NPC475605
0.8256	Intermediate Similarity	NPC474668
0.825	Intermediate Similarity	NPC101475
0.825	Intermediate Similarity	NPC31037
0.825	Intermediate Similarity	NPC157996
0.825	Intermediate Similarity	NPC34177
0.825	Intermediate Similarity	NPC40394
0.825	Intermediate Similarity	NPC90979
0.825	Intermediate Similarity	NPC472805
0.8235	Intermediate Similarity	NPC201273
0.8235	Intermediate Similarity	NPC139724
0.8235	Intermediate Similarity	NPC472986
0.8235	Intermediate Similarity	NPC472985
0.8235	Intermediate Similarity	NPC6605
0.8222	Intermediate Similarity	NPC227583
0.8222	Intermediate Similarity	NPC98457
0.8222	Intermediate Similarity	NPC12103
0.8214	Intermediate Similarity	NPC474047
0.8214	Intermediate Similarity	NPC185568
0.8214	Intermediate Similarity	NPC474493
0.8214	Intermediate Similarity	NPC238485
0.8205	Intermediate Similarity	NPC68443
0.8193	Intermediate Similarity	NPC202389
0.8193	Intermediate Similarity	NPC248886
0.8193	Intermediate Similarity	NPC304285
0.8193	Intermediate Similarity	NPC470049
0.8193	Intermediate Similarity	NPC30166
0.8171	Intermediate Similarity	NPC236707
0.8171	Intermediate Similarity	NPC281880
0.8171	Intermediate Similarity	NPC324772
0.8161	Intermediate Similarity	NPC477917
0.8161	Intermediate Similarity	NPC314727
0.8161	Intermediate Similarity	NPC16265
0.8161	Intermediate Similarity	NPC115607
0.8158	Intermediate Similarity	NPC266578
0.8158	Intermediate Similarity	NPC245795
0.8158	Intermediate Similarity	NPC471238
0.8158	Intermediate Similarity	NPC96484
0.8148	Intermediate Similarity	NPC300499
0.8148	Intermediate Similarity	NPC474989
0.8148	Intermediate Similarity	NPC99168
0.8148	Intermediate Similarity	NPC22955
0.8148	Intermediate Similarity	NPC31828
0.8148	Intermediate Similarity	NPC285761
0.8148	Intermediate Similarity	NPC474216
0.8148	Intermediate Similarity	NPC87604
0.8148	Intermediate Similarity	NPC470396
0.814	Intermediate Similarity	NPC476948
0.814	Intermediate Similarity	NPC470620
0.8133	Intermediate Similarity	NPC476406
0.8132	Intermediate Similarity	NPC261807
0.8125	Intermediate Similarity	NPC134330
0.8125	Intermediate Similarity	NPC120098
0.8125	Intermediate Similarity	NPC122418
0.8125	Intermediate Similarity	NPC274079
0.8125	Intermediate Similarity	NPC290598
0.8125	Intermediate Similarity	NPC244488
0.8125	Intermediate Similarity	NPC477925
0.8125	Intermediate Similarity	NPC247325
0.8125	Intermediate Similarity	NPC27765
0.8125	Intermediate Similarity	NPC30590
0.8125	Intermediate Similarity	NPC129165
0.8125	Intermediate Similarity	NPC189883
0.8125	Intermediate Similarity	NPC265328
0.8118	Intermediate Similarity	NPC266511

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 NPC249423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	179
0.1-0.2	1668
0.2-0.3	4007
0.3-0.4	2256
0.4-0.5	626
0.5-0.6	224
0.6-0.7	147
0.7-0.8	42
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
0.8272	Intermediate Similarity	NPD7645	Phase 2
0.8171	Intermediate Similarity	NPD6930	Phase 2
0.8171	Intermediate Similarity	NPD7514	Phase 3
0.8171	Intermediate Similarity	NPD6931	Approved
0.8171	Intermediate Similarity	NPD7332	Phase 2
0.8049	Intermediate Similarity	NPD6929	Approved
0.8	Intermediate Similarity	NPD8264	Approved
0.7952	Intermediate Similarity	NPD7525	Registered
0.7931	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7927	Intermediate Similarity	NPD7145	Approved
0.7882	Intermediate Similarity	NPD6695	Phase 3
0.7857	Intermediate Similarity	NPD6902	Approved
0.7805	Intermediate Similarity	NPD5776	Phase 2
0.7805	Intermediate Similarity	NPD6932	Approved
0.7805	Intermediate Similarity	NPD6925	Approved
0.7791	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7339	Approved
0.7778	Intermediate Similarity	NPD6942	Approved
0.7701	Intermediate Similarity	NPD6893	Approved
0.7683	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD6898	Phase 1
0.7528	Intermediate Similarity	NPD7524	Approved
0.7528	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD6926	Approved
0.7439	Intermediate Similarity	NPD6924	Approved
0.7412	Intermediate Similarity	NPD6683	Phase 2
0.7262	Intermediate Similarity	NPD6933	Approved
0.7229	Intermediate Similarity	NPD4784	Approved
0.7229	Intermediate Similarity	NPD4785	Approved
0.7222	Intermediate Similarity	NPD3618	Phase 1
0.7216	Intermediate Similarity	NPD7639	Approved
0.7216	Intermediate Similarity	NPD7640	Approved
0.7204	Intermediate Similarity	NPD6079	Approved
0.7204	Intermediate Similarity	NPD7087	Discontinued
0.7195	Intermediate Similarity	NPD7151	Approved
0.7195	Intermediate Similarity	NPD4243	Approved
0.7195	Intermediate Similarity	NPD7150	Approved
0.7195	Intermediate Similarity	NPD7152	Approved
0.7191	Intermediate Similarity	NPD4786	Approved
0.7174	Intermediate Similarity	NPD5328	Approved
0.7159	Intermediate Similarity	NPD3667	Approved
0.7143	Intermediate Similarity	NPD368	Approved
0.7126	Intermediate Similarity	NPD7509	Discontinued
0.7113	Intermediate Similarity	NPD7638	Approved
0.7108	Intermediate Similarity	NPD4732	Discontinued
0.7073	Intermediate Similarity	NPD7143	Approved
0.7073	Intermediate Similarity	NPD7144	Approved
0.7071	Intermediate Similarity	NPD5211	Phase 2
0.7021	Intermediate Similarity	NPD7637	Suspended
0.7021	Intermediate Similarity	NPD7515	Phase 2
0.6951	Remote Similarity	NPD6923	Approved
0.6951	Remote Similarity	NPD6922	Approved
0.6947	Remote Similarity	NPD4202	Approved
0.6932	Remote Similarity	NPD4748	Discontinued
0.6931	Remote Similarity	NPD5141	Approved
0.6915	Remote Similarity	NPD7136	Phase 2
0.6869	Remote Similarity	NPD5286	Approved
0.6869	Remote Similarity	NPD4696	Approved
0.6869	Remote Similarity	NPD5285	Approved
0.6848	Remote Similarity	NPD4623	Approved
0.6848	Remote Similarity	NPD4519	Discontinued
0.6837	Remote Similarity	NPD4755	Approved
0.6818	Remote Similarity	NPD4195	Approved
0.6813	Remote Similarity	NPD3133	Approved
0.6813	Remote Similarity	NPD3665	Phase 1
0.6813	Remote Similarity	NPD3666	Approved
0.68	Remote Similarity	NPD5344	Discontinued
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6768	Remote Similarity	NPD4225	Approved
0.6744	Remote Similarity	NPD4190	Phase 3
0.6744	Remote Similarity	NPD5275	Approved
0.6735	Remote Similarity	NPD5222	Approved
0.6735	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5221	Approved
0.6733	Remote Similarity	NPD5224	Approved
0.6733	Remote Similarity	NPD5226	Approved
0.6733	Remote Similarity	NPD5225	Approved
0.6733	Remote Similarity	NPD4633	Approved
0.6701	Remote Similarity	NPD7748	Approved
0.67	Remote Similarity	NPD4700	Approved
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD5173	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6634	Remote Similarity	NPD4159	Approved
0.6634	Remote Similarity	NPD5223	Approved
0.6632	Remote Similarity	NPD4753	Phase 2
0.6604	Remote Similarity	NPD4634	Approved
0.66	Remote Similarity	NPD5290	Discontinued
0.6579	Remote Similarity	NPD342	Phase 1
0.6571	Remote Similarity	NPD6899	Approved
0.6571	Remote Similarity	NPD6881	Approved
0.6569	Remote Similarity	NPD7632	Discontinued
0.6566	Remote Similarity	NPD4697	Phase 3
0.6559	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7115	Discovery
0.6538	Remote Similarity	NPD6402	Approved
0.6538	Remote Similarity	NPD5739	Approved
0.6538	Remote Similarity	NPD7128	Approved
0.6538	Remote Similarity	NPD6675	Approved
0.6535	Remote Similarity	NPD6648	Approved
0.6509	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.65	Remote Similarity	NPD7902	Approved
0.6495	Remote Similarity	NPD6411	Approved
0.6494	Remote Similarity	NPD4219	Approved
0.6489	Remote Similarity	NPD5279	Phase 3
0.6486	Remote Similarity	NPD7327	Approved
0.6486	Remote Similarity	NPD7328	Approved
0.6476	Remote Similarity	NPD5697	Approved
0.6465	Remote Similarity	NPD5210	Approved
0.6465	Remote Similarity	NPD4629	Approved
0.6458	Remote Similarity	NPD6051	Approved
0.6452	Remote Similarity	NPD3668	Phase 3
0.6449	Remote Similarity	NPD6883	Approved
0.6449	Remote Similarity	NPD7290	Approved
0.6449	Remote Similarity	NPD7102	Approved
0.6429	Remote Similarity	NPD6399	Phase 3
0.6429	Remote Similarity	NPD7516	Approved
0.6415	Remote Similarity	NPD4730	Approved
0.6415	Remote Similarity	NPD7320	Approved
0.6415	Remote Similarity	NPD4729	Approved
0.6413	Remote Similarity	NPD4221	Approved
0.6413	Remote Similarity	NPD4223	Phase 3
0.6389	Remote Similarity	NPD6869	Approved
0.6389	Remote Similarity	NPD6650	Approved
0.6389	Remote Similarity	NPD8130	Phase 1
0.6389	Remote Similarity	NPD6649	Approved
0.6389	Remote Similarity	NPD6847	Approved
0.6389	Remote Similarity	NPD6617	Approved
0.6383	Remote Similarity	NPD5329	Approved
0.6381	Remote Similarity	NPD4768	Approved
0.6381	Remote Similarity	NPD4767	Approved
0.6374	Remote Similarity	NPD4695	Discontinued
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6013	Approved
0.6355	Remote Similarity	NPD6014	Approved
0.6355	Remote Similarity	NPD6012	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6346	Remote Similarity	NPD4754	Approved
0.6337	Remote Similarity	NPD6083	Phase 2
0.6337	Remote Similarity	NPD6084	Phase 2
0.633	Remote Similarity	NPD6882	Approved
0.633	Remote Similarity	NPD8297	Approved
0.6321	Remote Similarity	NPD5701	Approved
0.6316	Remote Similarity	NPD8378	Approved
0.6316	Remote Similarity	NPD8296	Approved
0.6316	Remote Similarity	NPD8380	Approved
0.6316	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8379	Approved
0.6316	Remote Similarity	NPD7503	Approved
0.6316	Remote Similarity	NPD8335	Approved
0.6296	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD5250	Approved
0.6296	Remote Similarity	NPD5251	Approved
0.6296	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6101	Approved
0.6277	Remote Similarity	NPD4197	Approved
0.6273	Remote Similarity	NPD4632	Approved
0.6262	Remote Similarity	NPD5128	Approved
0.6262	Remote Similarity	NPD6686	Approved
0.6262	Remote Similarity	NPD6011	Approved
0.6262	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD5217	Approved
0.6239	Remote Similarity	NPD5216	Approved
0.6239	Remote Similarity	NPD5215	Approved
0.6228	Remote Similarity	NPD6054	Approved
0.6228	Remote Similarity	NPD7741	Discontinued
0.6228	Remote Similarity	NPD8377	Approved
0.6228	Remote Similarity	NPD8294	Approved
0.6226	Remote Similarity	NPD6640	Phase 3
0.6224	Remote Similarity	NPD3168	Discontinued
0.6211	Remote Similarity	NPD1696	Phase 3
0.62	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.62	Remote Similarity	NPD7900	Approved
0.6196	Remote Similarity	NPD4820	Approved
0.6196	Remote Similarity	NPD4822	Approved
0.6196	Remote Similarity	NPD4821	Approved
0.6196	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6196	Remote Similarity	NPD4819	Approved
0.6174	Remote Similarity	NPD8033	Approved
0.617	Remote Similarity	NPD4788	Approved
0.6168	Remote Similarity	NPD6412	Phase 2
0.6154	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5135	Approved
0.6147	Remote Similarity	NPD5169	Approved
0.6146	Remote Similarity	NPD4688	Approved
0.6146	Remote Similarity	NPD6684	Approved
0.6146	Remote Similarity	NPD5330	Approved
0.6146	Remote Similarity	NPD4693	Phase 3
0.6146	Remote Similarity	NPD7521	Approved
0.6146	Remote Similarity	NPD4138	Approved
0.6146	Remote Similarity	NPD7146	Approved
0.6146	Remote Similarity	NPD5205	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