NPASS Compound

Structure

CID312881 OpenBabel06191716122D 25 27 0 0 1 0 0 0 0 0999 V2000 0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -5.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -5.0000 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 3.4641 -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 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 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 2.5981 -3.5000 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 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 10 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 10 2 0 0 0 0 6 8 2 0 0 0 0 6 11 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 1 0 0 0 0 10 18 1 0 0 0 0 11 15 2 0 0 0 0 12 14 2 0 0 0 0 12 25 1 0 0 0 0 13 20 2 0 0 0 0 13 23 1 0 0 0 0 14 15 1 0 0 0 0 14 16 1 0 0 0 0 15 23 1 0 0 0 0 16 17 1 0 0 0 0 16 24 1 6 0 0 0 17 19 1 0 0 0 0 17 21 1 6 0 0 0 18 22 2 0 0 0 0 18 24 1 0 0 0 0 19 25 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.13
Volume:	345.797
LogP:	2.728
LogD:	2.78
LogS:	-3.517
# Rotatable Bonds:	3
TPSA:	85.97
# H-Bond Aceptor:	6
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.512
Synthetic Accessibility Score:	3.707
Fsp3:	0.368
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:	-4.785
MDCK Permeability:	4.026268652523868e-05
Pgp-inhibitor:	0.776
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.983

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.064
Plasma Protein Binding (PPB):	80.96942901611328%
Volume Distribution (VD):	1.442
Pgp-substrate:	12.133278846740723%

ADMET: Metabolism

CYP1A2-inhibitor:	0.463
CYP1A2-substrate:	0.825
CYP2C19-inhibitor:	0.777
CYP2C19-substrate:	0.332
CYP2C9-inhibitor:	0.831
CYP2C9-substrate:	0.412
CYP2D6-inhibitor:	0.636
CYP2D6-substrate:	0.232
CYP3A4-inhibitor:	0.581
CYP3A4-substrate:	0.41

ADMET: Excretion

Clearance (CL):	11.654
Half-life (T1/2):	0.51

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.956
Drug-inuced Liver Injury (DILI):	0.944
AMES Toxicity:	0.211
Rat Oral Acute Toxicity:	0.608
Maximum Recommended Daily Dose:	0.1
Skin Sensitization:	0.15
Carcinogencity:	0.876
Eye Corrosion:	0.004
Eye Irritation:	0.014
Respiratory Toxicity:	0.87

Download Data

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

Natural Product: NPC312881

Natural Product ID:	NPC312881
*Common Name:**	Laserpitin
IUPAC Name:	[(9S,10S)-9-hydroxy-8,8-dimethyl-2-oxo-9,10-dihydropyrano[2,3-f]chromen-10-yl] (Z)-2-methylbut-2-enoate
Synonyms:
Standard InCHIKey:	QPLSCFLMIOADPA-LNUYWUECSA-N
Standard InCHI:	InChI=1S/C19H20O6/c1-5-10(2)18(22)24-16-14-12(25-19(3,4)17(16)21)8-6-11-7-9-13(20)23-15(11)14/h5-9,16-17,21H,1-4H3/b10-5-/t16-,17-/m0/s1
SMILES:	C/C=C(C(=O)O[C@H]1c2c(ccc3c2oc(=O)cc3)OC([C@H]1O)(C)C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3402553
PubChem CID:	51396729
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0003484] Pyranocoumarins [CHEMONTID:0003485] Angular pyranocoumarins

*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
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	exudates	n.a.	n.a.	PMID[16441065]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[18558745]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21824777]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[22784551]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	root	n.a.	PMID[25068578]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	stems	n.a.	n.a.	PMID[25891102]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21056	Angelica keiskei	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15394	Angelica decursiva	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4340	Peucedanum praeruptorum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21056	Angelica keiskei	Species	Apiaceae	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
Others	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	Inhibition	<	50.0	%	PMID[559329]

☑ 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 NPC312881 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	353
0.1-0.2	1489
0.2-0.3	3675
0.3-0.4	8258
0.4-0.5	10300
0.5-0.6	4150
0.6-0.7	5718
0.7-0.8	5033
0.8-0.85	2780
0.85-0.9	716
0.9-0.95	153
0.95-1	72

Similarity Score	Similarity Level	Natural Product ID
0.9925	High Similarity	NPC152771
0.9925	High Similarity	NPC287286
0.9925	High Similarity	NPC195357
0.9848	High Similarity	NPC153818
0.9848	High Similarity	NPC155963
0.9848	High Similarity	NPC232246
0.9774	High Similarity	NPC151946
0.9774	High Similarity	NPC211110
0.9774	High Similarity	NPC279573
0.9773	High Similarity	NPC188380
0.9773	High Similarity	NPC224543
0.9773	High Similarity	NPC78746
0.9699	High Similarity	NPC294456
0.9699	High Similarity	NPC212124
0.9699	High Similarity	NPC184861
0.9699	High Similarity	NPC281014
0.9699	High Similarity	NPC225106
0.9697	High Similarity	NPC472525
0.9624	High Similarity	NPC38099
0.9624	High Similarity	NPC26954
0.9621	High Similarity	NPC18804
0.9621	High Similarity	NPC213173
0.9621	High Similarity	NPC47163
0.9621	High Similarity	NPC267412
0.9621	High Similarity	NPC260265
0.9621	High Similarity	NPC100986
0.9621	High Similarity	NPC164269
0.9621	High Similarity	NPC62366
0.9621	High Similarity	NPC224475
0.9621	High Similarity	NPC166672
0.9621	High Similarity	NPC180716
0.9621	High Similarity	NPC287182
0.9621	High Similarity	NPC74655
0.9621	High Similarity	NPC195343
0.9621	High Similarity	NPC127888
0.9621	High Similarity	NPC84894
0.9621	High Similarity	NPC319859
0.9621	High Similarity	NPC198381
0.9549	High Similarity	NPC86892
0.9549	High Similarity	NPC471625
0.9549	High Similarity	NPC471909
0.9549	High Similarity	NPC472424
0.9549	High Similarity	NPC281241
0.9545	High Similarity	NPC318400
0.9545	High Similarity	NPC207002
0.9545	High Similarity	NPC133956
0.9545	High Similarity	NPC471910
0.9545	High Similarity	NPC167111
0.9545	High Similarity	NPC296624
0.9493	High Similarity	NPC469701
0.9493	High Similarity	NPC85624
0.9478	High Similarity	NPC160727
0.9478	High Similarity	NPC283019
0.9478	High Similarity	NPC149320
0.9478	High Similarity	NPC177281
0.9478	High Similarity	NPC476455
0.9478	High Similarity	NPC128529
0.9478	High Similarity	NPC471630
0.9478	High Similarity	NPC55615
0.9474	High Similarity	NPC204353
0.9474	High Similarity	NPC326600
0.9474	High Similarity	NPC50896
0.9403	High Similarity	NPC33986
0.9398	High Similarity	NPC31849
0.9394	High Similarity	NPC29734
0.9357	High Similarity	NPC471764
0.9357	High Similarity	NPC87950
0.9357	High Similarity	NPC296377
0.9328	High Similarity	NPC253574
0.9328	High Similarity	NPC307412
0.9328	High Similarity	NPC98179
0.9328	High Similarity	NPC55149
0.9318	High Similarity	NPC113098
0.9291	High Similarity	NPC169510
0.9281	High Similarity	NPC471824
0.9254	High Similarity	NPC7526
0.9254	High Similarity	NPC222036
0.9248	High Similarity	NPC267336
0.9248	High Similarity	NPC272650
0.9179	High Similarity	NPC14248
0.9179	High Similarity	NPC194277
0.9167	High Similarity	NPC185066
0.9161	High Similarity	NPC103116
0.9124	High Similarity	NPC471068
0.9124	High Similarity	NPC471069
0.9118	High Similarity	NPC469675
0.9111	High Similarity	NPC469449
0.9098	High Similarity	NPC168710
0.9071	High Similarity	NPC183646
0.9071	High Similarity	NPC119640
0.9058	High Similarity	NPC471072
0.9058	High Similarity	NPC471071
0.9058	High Similarity	NPC471070
0.9051	High Similarity	NPC283331
0.903	High Similarity	NPC80170
0.9015	High Similarity	NPC471826
0.9007	High Similarity	NPC476457
0.9007	High Similarity	NPC471763
0.8971	High Similarity	NPC142563
0.8971	High Similarity	NPC241165
0.8971	High Similarity	NPC1220
0.8971	High Similarity	NPC163557
0.8971	High Similarity	NPC141822
0.8971	High Similarity	NPC291551
0.8971	High Similarity	NPC205797
0.8971	High Similarity	NPC469965
0.8947	High Similarity	NPC473993
0.8947	High Similarity	NPC258567
0.8947	High Similarity	NPC224774
0.8947	High Similarity	NPC121740
0.8929	High Similarity	NPC215512
0.8929	High Similarity	NPC279851
0.8929	High Similarity	NPC476442
0.8929	High Similarity	NPC472520
0.8929	High Similarity	NPC300611
0.8921	High Similarity	NPC35501
0.8921	High Similarity	NPC47040
0.8921	High Similarity	NPC37428
0.8921	High Similarity	NPC278600
0.8921	High Similarity	NPC137262
0.8921	High Similarity	NPC144512
0.8913	High Similarity	NPC103409
0.8905	High Similarity	NPC131950
0.8904	High Similarity	NPC470264
0.8881	High Similarity	NPC205361
0.8881	High Similarity	NPC199204
0.8881	High Similarity	NPC472519
0.8881	High Similarity	NPC469453
0.8864	High Similarity	NPC201667
0.8864	High Similarity	NPC111347
0.8864	High Similarity	NPC73413
0.8849	High Similarity	NPC131198
0.8844	High Similarity	NPC256141
0.8824	High Similarity	NPC103799
0.8819	High Similarity	NPC476347
0.8819	High Similarity	NPC15577
0.8811	High Similarity	NPC295696
0.8811	High Similarity	NPC226722
0.8806	High Similarity	NPC243688
0.8797	High Similarity	NPC471827
0.8797	High Similarity	NPC471828
0.8794	High Similarity	NPC138149
0.8788	High Similarity	NPC472518
0.8788	High Similarity	NPC109675
0.8788	High Similarity	NPC273772
0.8786	High Similarity	NPC270256
0.8759	High Similarity	NPC476348
0.8759	High Similarity	NPC187398
0.875	High Similarity	NPC32463
0.8741	High Similarity	NPC60704
0.8741	High Similarity	NPC293642
0.8741	High Similarity	NPC139595
0.8732	High Similarity	NPC184053
0.8732	High Similarity	NPC93640
0.8732	High Similarity	NPC20631
0.8731	High Similarity	NPC234109
0.8731	High Similarity	NPC188327
0.8722	High Similarity	NPC291899
0.8722	High Similarity	NPC27671
0.8712	High Similarity	NPC248429
0.8712	High Similarity	NPC96286
0.8707	High Similarity	NPC180351
0.8696	High Similarity	NPC469952
0.8696	High Similarity	NPC2363
0.8696	High Similarity	NPC469955
0.8696	High Similarity	NPC92805
0.869	High Similarity	NPC474302
0.8681	High Similarity	NPC108994
0.8681	High Similarity	NPC106126
0.8681	High Similarity	NPC475719
0.8681	High Similarity	NPC101255
0.8681	High Similarity	NPC43716
0.8671	High Similarity	NPC138212
0.8671	High Similarity	NPC229916
0.8662	High Similarity	NPC183642
0.8662	High Similarity	NPC310370
0.8662	High Similarity	NPC155552
0.8657	High Similarity	NPC232692
0.8657	High Similarity	NPC93219
0.8657	High Similarity	NPC202594
0.8657	High Similarity	NPC244495
0.8652	High Similarity	NPC43500
0.8652	High Similarity	NPC164148
0.8647	High Similarity	NPC50720
0.8647	High Similarity	NPC154176
0.8647	High Similarity	NPC173350
0.8647	High Similarity	NPC290605
0.8643	High Similarity	NPC262585
0.8643	High Similarity	NPC18189
0.8643	High Similarity	NPC20829
0.8639	High Similarity	NPC21184
0.8639	High Similarity	NPC120426
0.8639	High Similarity	NPC107197
0.8639	High Similarity	NPC205727
0.8639	High Similarity	NPC294522
0.8633	High Similarity	NPC124085
0.8633	High Similarity	NPC117048
0.863	High Similarity	NPC96294
0.863	High Similarity	NPC93924
0.8623	High Similarity	NPC19157

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 NPC312881 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	309
0.1-0.2	885
0.2-0.3	1782
0.3-0.4	2574
0.4-0.5	1982
0.5-0.6	1051
0.6-0.7	375
0.7-0.8	137
0.8-0.85	41
0.85-0.9	12
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8971	High Similarity	NPD5123	Clinical (unspecified phase)
0.8971	High Similarity	NPD5124	Phase 1
0.8794	High Similarity	NPD1652	Phase 2
0.8411	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8358	Intermediate Similarity	NPD422	Phase 1
0.8322	Intermediate Similarity	NPD1653	Approved
0.8247	Intermediate Similarity	NPD7075	Discontinued
0.8224	Intermediate Similarity	NPD6801	Discontinued
0.8212	Intermediate Similarity	NPD4380	Phase 2
0.8207	Intermediate Similarity	NPD2424	Discontinued
0.8099	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8099	Intermediate Similarity	NPD1613	Approved
0.8085	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.8085	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8013	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD5844	Phase 1
0.7973	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4908	Phase 1
0.7935	Intermediate Similarity	NPD7819	Suspended
0.7935	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD6799	Approved
0.7922	Intermediate Similarity	NPD7411	Suspended
0.7895	Intermediate Similarity	NPD5403	Approved
0.7881	Intermediate Similarity	NPD5401	Approved
0.7881	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7852	Intermediate Similarity	NPD3750	Approved
0.7852	Intermediate Similarity	NPD4628	Phase 3
0.7832	Intermediate Similarity	NPD6798	Discontinued
0.7826	Intermediate Similarity	NPD1610	Phase 2
0.7826	Intermediate Similarity	NPD1091	Approved
0.7823	Intermediate Similarity	NPD2796	Approved
0.7817	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7817	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD7097	Phase 1
0.7806	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7794	Intermediate Similarity	NPD1548	Phase 1
0.7791	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD8651	Approved
0.7785	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD5402	Approved
0.7771	Intermediate Similarity	NPD3817	Phase 2
0.7762	Intermediate Similarity	NPD3027	Phase 3
0.7758	Intermediate Similarity	NPD6559	Discontinued
0.7756	Intermediate Similarity	NPD1934	Approved
0.7755	Intermediate Similarity	NPD7033	Discontinued
0.7755	Intermediate Similarity	NPD3748	Approved
0.7746	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD6599	Discontinued
0.773	Intermediate Similarity	NPD2797	Approved
0.7724	Intermediate Similarity	NPD4060	Phase 1
0.7722	Intermediate Similarity	NPD7768	Phase 2
0.7718	Intermediate Similarity	NPD1549	Phase 2
0.7708	Intermediate Similarity	NPD1296	Phase 2
0.7708	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD8455	Phase 2
0.7687	Intermediate Similarity	NPD4536	Approved
0.7687	Intermediate Similarity	NPD4538	Approved
0.7687	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD6355	Discontinued
0.7667	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7662	Intermediate Similarity	NPD920	Approved
0.766	Intermediate Similarity	NPD3225	Approved
0.7658	Intermediate Similarity	NPD2415	Discontinued
0.7655	Intermediate Similarity	NPD6233	Phase 2
0.7651	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7639	Intermediate Similarity	NPD4625	Phase 3
0.7632	Intermediate Similarity	NPD5058	Phase 3
0.7589	Intermediate Similarity	NPD4749	Approved
0.7586	Intermediate Similarity	NPD3268	Approved
0.7576	Intermediate Similarity	NPD2684	Approved
0.7551	Intermediate Similarity	NPD4340	Discontinued
0.755	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD5762	Approved
0.7533	Intermediate Similarity	NPD6002	Phase 3
0.7533	Intermediate Similarity	NPD5763	Approved
0.7533	Intermediate Similarity	NPD6004	Phase 3
0.7533	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD6005	Phase 3
0.7533	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7517	Intermediate Similarity	NPD1510	Phase 2
0.7517	Intermediate Similarity	NPD4308	Phase 3
0.7517	Intermediate Similarity	NPD7095	Approved
0.7517	Intermediate Similarity	NPD5960	Phase 3
0.7517	Intermediate Similarity	NPD5588	Approved
0.7516	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7515	Intermediate Similarity	NPD3818	Discontinued
0.75	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3496	Discontinued
0.75	Intermediate Similarity	NPD7549	Discontinued
0.75	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD290	Approved
0.75	Intermediate Similarity	NPD1358	Approved
0.75	Intermediate Similarity	NPD6166	Phase 2
0.75	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2801	Approved
0.7484	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7482	Intermediate Similarity	NPD5691	Approved
0.7481	Intermediate Similarity	NPD7843	Approved
0.7481	Intermediate Similarity	NPD5535	Approved
0.747	Intermediate Similarity	NPD7054	Approved
0.7469	Intermediate Similarity	NPD5494	Approved
0.7467	Intermediate Similarity	NPD2935	Discontinued
0.7467	Intermediate Similarity	NPD1551	Phase 2
0.7466	Intermediate Similarity	NPD2313	Discontinued
0.7452	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7445	Intermediate Similarity	NPD7157	Approved
0.7429	Intermediate Similarity	NPD4626	Approved
0.7425	Intermediate Similarity	NPD7074	Phase 3
0.7425	Intermediate Similarity	NPD7472	Approved
0.7423	Intermediate Similarity	NPD7199	Phase 2
0.7421	Intermediate Similarity	NPD37	Approved
0.7421	Intermediate Similarity	NPD4433	Discontinued
0.7417	Intermediate Similarity	NPD7266	Discontinued
0.7407	Intermediate Similarity	NPD919	Approved
0.7403	Intermediate Similarity	NPD6667	Approved
0.7403	Intermediate Similarity	NPD6666	Approved
0.74	Intermediate Similarity	NPD2799	Discontinued
0.7396	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4967	Phase 2
0.7391	Intermediate Similarity	NPD4966	Approved
0.7391	Intermediate Similarity	NPD4965	Approved
0.7381	Intermediate Similarity	NPD6797	Phase 2
0.7379	Intermediate Similarity	NPD2861	Phase 2
0.7375	Intermediate Similarity	NPD1465	Phase 2
0.7368	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4307	Phase 2
0.7365	Intermediate Similarity	NPD4140	Approved
0.7361	Intermediate Similarity	NPD3267	Approved
0.7361	Intermediate Similarity	NPD3266	Approved
0.7355	Intermediate Similarity	NPD1511	Approved
0.7348	Intermediate Similarity	NPD9697	Approved
0.7347	Intermediate Similarity	NPD7985	Registered
0.7346	Intermediate Similarity	NPD3749	Approved
0.7342	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7337	Intermediate Similarity	NPD7251	Discontinued
0.7329	Intermediate Similarity	NPD6832	Phase 2
0.732	Intermediate Similarity	NPD6674	Discontinued
0.7317	Intermediate Similarity	NPD8127	Discontinued
0.7308	Intermediate Similarity	NPD2532	Approved
0.7308	Intermediate Similarity	NPD2534	Approved
0.7308	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD2533	Approved
0.7305	Intermediate Similarity	NPD1778	Approved
0.7301	Intermediate Similarity	NPD6234	Discontinued
0.7297	Intermediate Similarity	NPD4062	Phase 3
0.7294	Intermediate Similarity	NPD7808	Phase 3
0.7293	Intermediate Similarity	NPD3134	Approved
0.7284	Intermediate Similarity	NPD3882	Suspended
0.7273	Intermediate Similarity	NPD9717	Approved
0.7273	Intermediate Similarity	NPD7229	Phase 3
0.7273	Intermediate Similarity	NPD6232	Discontinued
0.7267	Intermediate Similarity	NPD6653	Approved
0.7261	Intermediate Similarity	NPD1512	Approved
0.7248	Intermediate Similarity	NPD1240	Approved
0.7244	Intermediate Similarity	NPD7212	Phase 2
0.7244	Intermediate Similarity	NPD7213	Phase 3
0.7237	Intermediate Similarity	NPD6099	Approved
0.7237	Intermediate Similarity	NPD6100	Approved
0.7237	Intermediate Similarity	NPD6032	Approved
0.7229	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7226	Intermediate Similarity	NPD6190	Approved
0.7213	Intermediate Similarity	NPD7583	Approved
0.7212	Intermediate Similarity	NPD6959	Discontinued
0.7202	Intermediate Similarity	NPD7228	Approved
0.7202	Intermediate Similarity	NPD3751	Discontinued
0.72	Intermediate Similarity	NPD447	Suspended
0.72	Intermediate Similarity	NPD230	Phase 1
0.7197	Intermediate Similarity	NPD7447	Phase 1
0.7194	Intermediate Similarity	NPD6671	Approved
0.7192	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD2346	Discontinued
0.7174	Intermediate Similarity	NPD7585	Approved
0.7169	Intermediate Similarity	NPD3787	Discontinued
0.7161	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD4535	Phase 3
0.7152	Intermediate Similarity	NPD1607	Approved
0.7152	Intermediate Similarity	NPD5049	Phase 3
0.7152	Intermediate Similarity	NPD6273	Approved
0.7143	Intermediate Similarity	NPD7473	Discontinued
0.7125	Intermediate Similarity	NPD3226	Approved
0.7124	Intermediate Similarity	NPD4477	Approved
0.7124	Intermediate Similarity	NPD4476	Approved
0.7123	Intermediate Similarity	NPD987	Approved
0.7123	Intermediate Similarity	NPD1203	Approved
0.7117	Intermediate Similarity	NPD4288	Approved
0.7114	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD2800	Approved
0.7095	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD1933	Approved
0.7083	Intermediate Similarity	NPD1611	Approved
0.7078	Intermediate Similarity	NPD2343	Clinical (unspecified phase)

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