NPASS Compound

Structure

NPC472497 OpenBabel07101719152D 23 26 0 0 1 0 0 0 0 0999 V2000 -1.4576 2.1380 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3709 0.2141 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2424 1.5801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 2.1603 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8709 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.8002 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2650 1.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9195 -0.3930 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0646 1.2185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5775 0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5630 1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2472 0.7201 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6236 -0.3600 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.7201 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0896 0.9960 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.8709 1.0801 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 1.0801 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 -0.3405 2.1440 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6236 -1.3600 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6634 1.6539 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 18 1 0 0 0 0 7 19 1 0 0 0 0 8 13 1 0 0 0 0 9 14 1 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 11 12 1 0 0 0 0 11 17 1 0 0 0 0 12 8 1 1 0 0 0 13 16 1 0 0 0 0 13 21 2 0 0 0 0 14 18 1 0 0 0 0 14 19 1 1 0 0 0 15 20 1 1 0 0 0 15 22 1 0 0 0 0 16 19 1 1 0 0 0 16 20 1 0 0 0 0 17 20 1 1 0 0 0 17 23 1 0 0 0 0 19 4 1 1 0 0 0 20 10 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	318.22
Volume:	341.348
LogP:	2.785
LogD:	2.605
LogS:	-3.949
# Rotatable Bonds:	0
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.675
Synthetic Accessibility Score:	5.973
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.831
MDCK Permeability:	4.584989437717013e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.888
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.565
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.51
Plasma Protein Binding (PPB):	53.868263244628906%
Volume Distribution (VD):	1.261
Pgp-substrate:	53.569793701171875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.248
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.773
CYP2C9-inhibitor:	0.128
CYP2C9-substrate:	0.319
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.472
CYP3A4-inhibitor:	0.125
CYP3A4-substrate:	0.164

ADMET: Excretion

Clearance (CL):	5.99
Half-life (T1/2):	0.254

ADMET: Toxicity

hERG Blockers:	0.034
Human Hepatotoxicity (H-HT):	0.39
Drug-inuced Liver Injury (DILI):	0.307
AMES Toxicity:	0.284
Rat Oral Acute Toxicity:	0.964
Maximum Recommended Daily Dose:	0.996
Skin Sensitization:	0.364
Carcinogencity:	0.043
Eye Corrosion:	0.484
Eye Irritation:	0.768
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC472497

Natural Product ID:	NPC472497
*Common Name:**	VFEDAJWXUVNGTR-JMKUXKBGSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VFEDAJWXUVNGTR-JMKUXKBGSA-N
Standard InCHI:	InChI=1S/C20H30O3/c1-11-12-8-13(21)16-19(4)7-5-6-18(2,3)14(19)9-15(22)20(16,10-12)17(11)23/h12,14-17,22-23H,1,5-10H2,2-4H3/t12-,14-,15-,16+,17-,19-,20+/m1/s1
SMILES:	CC1(CCCC2(C1CC(C34C2C(=O)CC(C3)C(=C)C4O)O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3426509
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0003782] Kaurane 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
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	Eukaryota	n.a.	Guangxi Zhuang Autonomous Region, China	n.a.	PMID[25856683]
NPO20739	Jungermannia hyalina	Species	Jungermanniaceae	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	14

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	7
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	>	50000.0	nM	PMID[505417]
NPT2410	Cell Line	NCI-H1299	Homo sapiens	IC50	>	50000.0	nM	PMID[505417]
NPT114	Cell Line	LoVo	Homo sapiens	IC50	>	50000.0	nM	PMID[505417]
NPT111	Cell Line	K562	Homo sapiens	IC50	>	50000.0	nM	PMID[505417]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	>	50000.0	nM	PMID[505417]
NPT858	Cell Line	LNCaP	Homo sapiens	IC50	>	50000.0	nM	PMID[505417]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	50000.0	nM	PMID[505417]
NPT27	Others	Unspecified		IC50	>	50000.0	nM	PMID[505417]

☑ 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 NPC472497 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	184
0.1-0.2	1619
0.2-0.3	6311
0.3-0.4	15302
0.4-0.5	7145
0.5-0.6	5504
0.6-0.7	4659
0.7-0.8	1702
0.8-0.85	192
0.85-0.9	68
0.9-0.95	8
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC472495
0.9506	High Similarity	NPC472498
0.9419	High Similarity	NPC472496
0.9412	High Similarity	NPC100313
0.931	High Similarity	NPC280804
0.9157	High Similarity	NPC146683
0.9059	High Similarity	NPC174619
0.9059	High Similarity	NPC4643
0.9036	High Similarity	NPC118800
0.8966	High Similarity	NPC180849
0.8941	High Similarity	NPC472738
0.8916	High Similarity	NPC46881
0.8837	High Similarity	NPC165895
0.8837	High Similarity	NPC153604
0.8824	High Similarity	NPC292553
0.8764	High Similarity	NPC144739
0.8764	High Similarity	NPC59170
0.8764	High Similarity	NPC181594
0.8764	High Similarity	NPC59350
0.871	High Similarity	NPC121218
0.871	High Similarity	NPC253886
0.871	High Similarity	NPC295276
0.8706	High Similarity	NPC475745
0.8706	High Similarity	NPC474482
0.869	High Similarity	NPC170985
0.869	High Similarity	NPC110780
0.8675	High Similarity	NPC164999
0.8667	High Similarity	NPC91772
0.8667	High Similarity	NPC129004
0.8667	High Similarity	NPC111524
0.8667	High Similarity	NPC29247
0.8667	High Similarity	NPC104371
0.8667	High Similarity	NPC101233
0.8667	High Similarity	NPC289539
0.8667	High Similarity	NPC153775
0.8667	High Similarity	NPC261333
0.8667	High Similarity	NPC215271
0.8667	High Similarity	NPC292374
0.8652	High Similarity	NPC476168
0.8652	High Similarity	NPC299185
0.8621	High Similarity	NPC57469
0.8605	High Similarity	NPC102292
0.8588	High Similarity	NPC471036
0.8588	High Similarity	NPC291320
0.8588	High Similarity	NPC472743
0.8588	High Similarity	NPC475726
0.8571	High Similarity	NPC164210
0.8571	High Similarity	NPC29112
0.8571	High Similarity	NPC138245
0.8571	High Similarity	NPC231060
0.8571	High Similarity	NPC84018
0.8556	High Similarity	NPC294263
0.8539	High Similarity	NPC470378
0.8539	High Similarity	NPC261994
0.8539	High Similarity	NPC149761
0.8539	High Similarity	NPC80401
0.8537	High Similarity	NPC260301
0.8537	High Similarity	NPC307336
0.8488	Intermediate Similarity	NPC263974
0.8478	Intermediate Similarity	NPC264979
0.8478	Intermediate Similarity	NPC140242
0.8478	Intermediate Similarity	NPC13949
0.8478	Intermediate Similarity	NPC135548
0.8471	Intermediate Similarity	NPC145143
0.8471	Intermediate Similarity	NPC477858
0.8462	Intermediate Similarity	NPC302008
0.8462	Intermediate Similarity	NPC191094
0.8444	Intermediate Similarity	NPC278106
0.8438	Intermediate Similarity	NPC47281
0.8434	Intermediate Similarity	NPC472501
0.8421	Intermediate Similarity	NPC170615
0.8409	Intermediate Similarity	NPC259009
0.8391	Intermediate Similarity	NPC76518
0.8391	Intermediate Similarity	NPC190704
0.8391	Intermediate Similarity	NPC471034
0.8353	Intermediate Similarity	NPC103754
0.8353	Intermediate Similarity	NPC474484
0.8352	Intermediate Similarity	NPC244356
0.8352	Intermediate Similarity	NPC224060
0.8352	Intermediate Similarity	NPC82138
0.8351	Intermediate Similarity	NPC37600
0.8351	Intermediate Similarity	NPC50535
0.8333	Intermediate Similarity	NPC266
0.8333	Intermediate Similarity	NPC476316
0.8333	Intermediate Similarity	NPC46758
0.8315	Intermediate Similarity	NPC16377
0.8315	Intermediate Similarity	NPC328539
0.8315	Intermediate Similarity	NPC472739
0.8315	Intermediate Similarity	NPC474719
0.8313	Intermediate Similarity	NPC106078
0.8313	Intermediate Similarity	NPC138502
0.8295	Intermediate Similarity	NPC469994
0.828	Intermediate Similarity	NPC234564
0.8276	Intermediate Similarity	NPC74595
0.8276	Intermediate Similarity	NPC474233
0.8276	Intermediate Similarity	NPC264665
0.8261	Intermediate Similarity	NPC64006
0.8242	Intermediate Similarity	NPC198242
0.8242	Intermediate Similarity	NPC250753
0.8242	Intermediate Similarity	NPC63748
0.8242	Intermediate Similarity	NPC211403
0.8229	Intermediate Similarity	NPC477915
0.8222	Intermediate Similarity	NPC472970
0.8222	Intermediate Similarity	NPC472971
0.8214	Intermediate Similarity	NPC472500
0.8214	Intermediate Similarity	NPC472499
0.8211	Intermediate Similarity	NPC156324
0.8211	Intermediate Similarity	NPC127408
0.8211	Intermediate Similarity	NPC55503
0.8211	Intermediate Similarity	NPC291785
0.8202	Intermediate Similarity	NPC269360
0.8202	Intermediate Similarity	NPC264005
0.8193	Intermediate Similarity	NPC472487
0.8193	Intermediate Similarity	NPC472486
0.8193	Intermediate Similarity	NPC38141
0.8191	Intermediate Similarity	NPC18509
0.8191	Intermediate Similarity	NPC10864
0.8191	Intermediate Similarity	NPC190554
0.8182	Intermediate Similarity	NPC294438
0.8182	Intermediate Similarity	NPC264317
0.8182	Intermediate Similarity	NPC474218
0.8172	Intermediate Similarity	NPC266431
0.8172	Intermediate Similarity	NPC210214
0.8172	Intermediate Similarity	NPC98639
0.8163	Intermediate Similarity	NPC28791
0.8163	Intermediate Similarity	NPC295366
0.8161	Intermediate Similarity	NPC245866
0.8152	Intermediate Similarity	NPC477520
0.8152	Intermediate Similarity	NPC69454
0.8144	Intermediate Similarity	NPC470310
0.8144	Intermediate Similarity	NPC469985
0.814	Intermediate Similarity	NPC328264
0.814	Intermediate Similarity	NPC157655
0.8125	Intermediate Similarity	NPC60947
0.8125	Intermediate Similarity	NPC289148
0.8125	Intermediate Similarity	NPC52899
0.8125	Intermediate Similarity	NPC39683
0.8125	Intermediate Similarity	NPC471790
0.8125	Intermediate Similarity	NPC163963
0.8118	Intermediate Similarity	NPC5604
0.8118	Intermediate Similarity	NPC201459
0.8118	Intermediate Similarity	NPC24504
0.8111	Intermediate Similarity	NPC146937
0.8111	Intermediate Similarity	NPC193360
0.8111	Intermediate Similarity	NPC131470
0.8111	Intermediate Similarity	NPC471900
0.8111	Intermediate Similarity	NPC143767
0.8105	Intermediate Similarity	NPC89099
0.8105	Intermediate Similarity	NPC20479
0.8105	Intermediate Similarity	NPC38471
0.8105	Intermediate Similarity	NPC98837
0.8105	Intermediate Similarity	NPC162459
0.8105	Intermediate Similarity	NPC38296
0.8105	Intermediate Similarity	NPC28864
0.8095	Intermediate Similarity	NPC472746
0.809	Intermediate Similarity	NPC70661
0.809	Intermediate Similarity	NPC2783
0.809	Intermediate Similarity	NPC80590
0.809	Intermediate Similarity	NPC34190
0.809	Intermediate Similarity	NPC12774
0.809	Intermediate Similarity	NPC269396
0.809	Intermediate Similarity	NPC98236
0.8085	Intermediate Similarity	NPC29410
0.8085	Intermediate Similarity	NPC49371
0.8085	Intermediate Similarity	NPC200054
0.8085	Intermediate Similarity	NPC104568
0.8081	Intermediate Similarity	NPC477916
0.8081	Intermediate Similarity	NPC251824
0.8081	Intermediate Similarity	NPC86852
0.8081	Intermediate Similarity	NPC83744
0.8072	Intermediate Similarity	NPC185536
0.8072	Intermediate Similarity	NPC125767
0.8072	Intermediate Similarity	NPC21220
0.8068	Intermediate Similarity	NPC227132
0.8068	Intermediate Similarity	NPC82902
0.8065	Intermediate Similarity	NPC209662
0.8065	Intermediate Similarity	NPC470385
0.8065	Intermediate Similarity	NPC470386
0.8065	Intermediate Similarity	NPC303863
0.8061	Intermediate Similarity	NPC204833
0.8061	Intermediate Similarity	NPC209502
0.8049	Intermediate Similarity	NPC472506
0.8046	Intermediate Similarity	NPC317066
0.8043	Intermediate Similarity	NPC168027
0.8043	Intermediate Similarity	NPC185936
0.8041	Intermediate Similarity	NPC246736
0.8041	Intermediate Similarity	NPC76866
0.8041	Intermediate Similarity	NPC214946
0.8041	Intermediate Similarity	NPC304832
0.8041	Intermediate Similarity	NPC148628
0.8041	Intermediate Similarity	NPC88203
0.8041	Intermediate Similarity	NPC475803
0.8041	Intermediate Similarity	NPC286519
0.8041	Intermediate Similarity	NPC309388
0.8023	Intermediate Similarity	NPC47149
0.8022	Intermediate Similarity	NPC275740
0.8022	Intermediate Similarity	NPC473999
0.8022	Intermediate Similarity	NPC86319
0.8022	Intermediate Similarity	NPC2983
0.8022	Intermediate Similarity	NPC477943

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 NPC472497 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	174
0.1-0.2	2076
0.2-0.3	4260
0.3-0.4	1806
0.4-0.5	403
0.5-0.6	155
0.6-0.7	151
0.7-0.8	119
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
0.8229	Intermediate Similarity	NPD5211	Phase 2
0.8222	Intermediate Similarity	NPD5328	Approved
0.8191	Intermediate Similarity	NPD4755	Approved
0.8182	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD4788	Approved
0.809	Intermediate Similarity	NPD3618	Phase 1
0.8061	Intermediate Similarity	NPD5141	Approved
0.8043	Intermediate Similarity	NPD6079	Approved
0.8021	Intermediate Similarity	NPD4700	Approved
0.8021	Intermediate Similarity	NPD5285	Approved
0.8021	Intermediate Similarity	NPD5286	Approved
0.8021	Intermediate Similarity	NPD4696	Approved
0.7957	Intermediate Similarity	NPD4202	Approved
0.7895	Intermediate Similarity	NPD4697	Phase 3
0.7865	Intermediate Similarity	NPD3133	Approved
0.7865	Intermediate Similarity	NPD4786	Approved
0.7865	Intermediate Similarity	NPD3666	Approved
0.7865	Intermediate Similarity	NPD3665	Phase 1
0.7857	Intermediate Similarity	NPD5224	Approved
0.7857	Intermediate Similarity	NPD3703	Phase 2
0.7857	Intermediate Similarity	NPD5226	Approved
0.7857	Intermediate Similarity	NPD5225	Approved
0.7857	Intermediate Similarity	NPD4633	Approved
0.7841	Intermediate Similarity	NPD3667	Approved
0.7778	Intermediate Similarity	NPD5174	Approved
0.7778	Intermediate Similarity	NPD5175	Approved
0.7755	Intermediate Similarity	NPD5223	Approved
0.7711	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7708	Intermediate Similarity	NPD5221	Approved
0.7708	Intermediate Similarity	NPD5222	Approved
0.7683	Intermediate Similarity	NPD3698	Phase 2
0.7683	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD8034	Phase 2
0.766	Intermediate Similarity	NPD8035	Phase 2
0.7634	Intermediate Similarity	NPD4753	Phase 2
0.7629	Intermediate Similarity	NPD5173	Approved
0.7624	Intermediate Similarity	NPD6675	Approved
0.7624	Intermediate Similarity	NPD5739	Approved
0.7624	Intermediate Similarity	NPD7128	Approved
0.7624	Intermediate Similarity	NPD4767	Approved
0.7624	Intermediate Similarity	NPD4768	Approved
0.7624	Intermediate Similarity	NPD6402	Approved
0.76	Intermediate Similarity	NPD4754	Approved
0.759	Intermediate Similarity	NPD4245	Approved
0.759	Intermediate Similarity	NPD4244	Approved
0.7573	Intermediate Similarity	NPD6373	Approved
0.7573	Intermediate Similarity	NPD6372	Approved
0.7549	Intermediate Similarity	NPD5701	Approved
0.7549	Intermediate Similarity	NPD5697	Approved
0.7476	Intermediate Similarity	NPD6899	Approved
0.7476	Intermediate Similarity	NPD5128	Approved
0.7476	Intermediate Similarity	NPD4729	Approved
0.7476	Intermediate Similarity	NPD6881	Approved
0.7476	Intermediate Similarity	NPD7320	Approved
0.7476	Intermediate Similarity	NPD4730	Approved
0.7444	Intermediate Similarity	NPD4221	Approved
0.7444	Intermediate Similarity	NPD4223	Phase 3
0.7429	Intermediate Similarity	NPD6650	Approved
0.7429	Intermediate Similarity	NPD6649	Approved
0.7423	Intermediate Similarity	NPD5210	Approved
0.7423	Intermediate Similarity	NPD4629	Approved
0.7404	Intermediate Similarity	NPD6012	Approved
0.7404	Intermediate Similarity	NPD6013	Approved
0.7404	Intermediate Similarity	NPD6014	Approved
0.7356	Intermediate Similarity	NPD6117	Approved
0.7333	Intermediate Similarity	NPD5251	Approved
0.7333	Intermediate Similarity	NPD7290	Approved
0.7333	Intermediate Similarity	NPD5249	Phase 3
0.7333	Intermediate Similarity	NPD5250	Approved
0.7333	Intermediate Similarity	NPD4634	Approved
0.7333	Intermediate Similarity	NPD7102	Approved
0.7333	Intermediate Similarity	NPD6883	Approved
0.7333	Intermediate Similarity	NPD5247	Approved
0.7333	Intermediate Similarity	NPD5248	Approved
0.7326	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD6011	Approved
0.7292	Intermediate Similarity	NPD7515	Phase 2
0.7283	Intermediate Similarity	NPD4197	Approved
0.7273	Intermediate Similarity	NPD6116	Phase 1
0.7264	Intermediate Similarity	NPD5216	Approved
0.7264	Intermediate Similarity	NPD5215	Approved
0.7264	Intermediate Similarity	NPD5217	Approved
0.7264	Intermediate Similarity	NPD6869	Approved
0.7264	Intermediate Similarity	NPD6847	Approved
0.7264	Intermediate Similarity	NPD8130	Phase 1
0.7264	Intermediate Similarity	NPD6617	Approved
0.7222	Intermediate Similarity	NPD7525	Registered
0.7216	Intermediate Similarity	NPD6399	Phase 3
0.7204	Intermediate Similarity	NPD5329	Approved
0.7196	Intermediate Similarity	NPD8297	Approved
0.7196	Intermediate Similarity	NPD6882	Approved
0.7195	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6115	Approved
0.7191	Intermediate Similarity	NPD6118	Approved
0.7191	Intermediate Similarity	NPD6114	Approved
0.7191	Intermediate Similarity	NPD6697	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.717	Intermediate Similarity	NPD5169	Approved
0.717	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5135	Approved
0.7159	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5360	Phase 3
0.7143	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD7640	Approved
0.7129	Intermediate Similarity	NPD7639	Approved
0.7128	Intermediate Similarity	NPD4138	Approved
0.7128	Intermediate Similarity	NPD4693	Phase 3
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7128	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD5205	Approved
0.7128	Intermediate Similarity	NPD4689	Approved
0.7128	Intermediate Similarity	NPD4690	Approved
0.7128	Intermediate Similarity	NPD4688	Approved
0.7103	Intermediate Similarity	NPD5127	Approved
0.7103	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.71	Intermediate Similarity	NPD6083	Phase 2
0.71	Intermediate Similarity	NPD6084	Phase 2
0.7097	Intermediate Similarity	NPD3668	Phase 3
0.703	Intermediate Similarity	NPD7638	Approved
0.703	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD3671	Phase 1
0.7	Intermediate Similarity	NPD6274	Approved
0.6981	Remote Similarity	NPD5168	Approved
0.6979	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD4632	Approved
0.697	Remote Similarity	NPD7748	Approved
0.6957	Remote Similarity	NPD4139	Approved
0.6957	Remote Similarity	NPD4692	Approved
0.6952	Remote Similarity	NPD6008	Approved
0.6947	Remote Similarity	NPD5280	Approved
0.6947	Remote Similarity	NPD7334	Approved
0.6947	Remote Similarity	NPD6684	Approved
0.6947	Remote Similarity	NPD4694	Approved
0.6947	Remote Similarity	NPD6409	Approved
0.6947	Remote Similarity	NPD5690	Phase 2
0.6947	Remote Similarity	NPD7521	Approved
0.6947	Remote Similarity	NPD5330	Approved
0.6947	Remote Similarity	NPD7146	Approved
0.6931	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD7645	Phase 2
0.6909	Remote Similarity	NPD5167	Approved
0.6905	Remote Similarity	NPD4224	Phase 2
0.69	Remote Similarity	NPD5695	Phase 3
0.6897	Remote Similarity	NPD4758	Discontinued
0.6875	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7339	Approved
0.6854	Remote Similarity	NPD3702	Approved
0.6854	Remote Similarity	NPD6942	Approved
0.6814	Remote Similarity	NPD7101	Approved
0.6814	Remote Similarity	NPD7100	Approved
0.6813	Remote Similarity	NPD3617	Approved
0.6804	Remote Similarity	NPD6903	Approved
0.6786	Remote Similarity	NPD7115	Discovery
0.6786	Remote Similarity	NPD6009	Approved
0.6786	Remote Similarity	NPD6317	Approved
0.6771	Remote Similarity	NPD4623	Approved
0.6771	Remote Similarity	NPD4519	Discontinued
0.6768	Remote Similarity	NPD5284	Approved
0.6768	Remote Similarity	NPD5281	Approved
0.6754	Remote Similarity	NPD6059	Approved
0.6754	Remote Similarity	NPD6054	Approved
0.6754	Remote Similarity	NPD6319	Approved
0.6739	Remote Similarity	NPD4195	Approved
0.6733	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6335	Approved
0.6726	Remote Similarity	NPD6313	Approved
0.6726	Remote Similarity	NPD6314	Approved
0.6705	Remote Similarity	NPD5777	Approved
0.6696	Remote Similarity	NPD6909	Approved
0.6696	Remote Similarity	NPD6908	Approved
0.6696	Remote Similarity	NPD6015	Approved
0.6696	Remote Similarity	NPD6016	Approved
0.6696	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD8133	Approved
0.6667	Remote Similarity	NPD4748	Discontinued
0.6638	Remote Similarity	NPD6370	Approved
0.6638	Remote Similarity	NPD5988	Approved
0.6634	Remote Similarity	NPD7900	Approved
0.6634	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD6001	Approved
0.661	Remote Similarity	NPD7507	Approved
0.6598	Remote Similarity	NPD6098	Approved
0.6591	Remote Similarity	NPD4787	Phase 1
0.6574	Remote Similarity	NPD6412	Phase 2
0.6559	Remote Similarity	NPD6929	Approved
0.6552	Remote Similarity	NPD5983	Phase 2
0.6549	Remote Similarity	NPD6868	Approved
0.6538	Remote Similarity	NPD4225	Approved
0.6531	Remote Similarity	NPD3573	Approved
0.6525	Remote Similarity	NPD7492	Approved
0.6517	Remote Similarity	NPD4243	Approved
0.6517	Remote Similarity	NPD6081	Approved
0.65	Remote Similarity	NPD7736	Approved
0.65	Remote Similarity	NPD4096	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