NPASS Compound

Structure

NPC241165 OpenBabel07101718182D 27 30 0 0 1 0 0 0 0 0999 V2000 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -1.0000 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 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 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 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 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 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 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 1 0 0 0 0 4 22 1 0 0 0 0 5 22 1 0 0 0 0 6 7 1 0 0 0 0 7 13 1 0 0 0 0 8 9 2 0 0 0 0 8 14 1 0 0 0 0 9 22 1 0 0 0 0 10 13 2 0 0 0 0 10 15 1 0 0 0 0 11 2 1 6 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 3 1 1 0 0 0 12 25 1 0 0 0 0 13 16 1 0 0 0 0 14 19 2 0 0 0 0 14 20 1 0 0 0 0 15 23 2 0 0 0 0 15 26 1 0 0 0 0 16 20 2 0 0 0 0 16 21 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 17 21 2 0 0 0 0 18 24 1 6 0 0 0 19 25 1 0 0 0 0 20 27 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	370.18
Volume:	382.975
LogP:	5.035
LogD:	4.39
LogS:	-3.819
# Rotatable Bonds:	2
TPSA:	68.9
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.795
Synthetic Accessibility Score:	4.171
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.742
MDCK Permeability:	1.4403538443730213e-05
Pgp-inhibitor:	0.989
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.025
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.007

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.054
Plasma Protein Binding (PPB):	94.21195220947266%
Volume Distribution (VD):	1.507
Pgp-substrate:	6.122225761413574%

ADMET: Metabolism

CYP1A2-inhibitor:	0.549
CYP1A2-substrate:	0.842
CYP2C19-inhibitor:	0.716
CYP2C19-substrate:	0.663
CYP2C9-inhibitor:	0.827
CYP2C9-substrate:	0.881
CYP2D6-inhibitor:	0.785
CYP2D6-substrate:	0.265
CYP3A4-inhibitor:	0.53
CYP3A4-substrate:	0.227

ADMET: Excretion

Clearance (CL):	1.828
Half-life (T1/2):	0.193

ADMET: Toxicity

hERG Blockers:	0.026
Human Hepatotoxicity (H-HT):	0.88
Drug-inuced Liver Injury (DILI):	0.9
AMES Toxicity:	0.105
Rat Oral Acute Toxicity:	0.918
Maximum Recommended Daily Dose:	0.593
Skin Sensitization:	0.194
Carcinogencity:	0.881
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.177

Download Data

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

Natural Product: NPC241165

Natural Product ID:	NPC241165
*Common Name:**	(+)-Calanolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	NIDRYBLTWYFCFV-SEDUGSJDSA-N
Standard InCHI:	InChI=1S/C22H26O5/c1-6-7-13-10-15(23)26-21-16(13)20-14(8-9-22(4,5)27-20)19-17(21)18(24)11(2)12(3)25-19/h8-12,18,24H,6-7H2,1-5H3/t11-,12-,18-/m1/s1
SMILES:	CCCc1cc(=O)oc2c1c1OC(C)(C)C=Cc1c1c2[C@H](O)[C@@H]([C@H](O1)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL7121
PubChem CID:	65008
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
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	Sarawak, Malaysia	n.a.	PMID[11430019]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1379639]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	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
EC50	1
IC50	1
Ki	6
Others	2

Activity Type	# Activity
Cell Line	3
Individual Protein	6
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	Max protection	=	100.0	%	PMID[511963]
NPT315	Cell Line	CEM-SS	Homo sapiens	EC50	=	400.0	nM	PMID[511963]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	15000.0	nM	PMID[511963]
NPT233	Individual Protein	Carbonic anhydrase II	Homo sapiens	Ki	=	50700.0	nM	PMID[511965]
NPT3101	Individual Protein	Carbonic anhydrase XIII	Homo sapiens	Ki	=	21000.0	nM	PMID[511965]
NPT27	Others	Unspecified		Therapeutic indices	=	37.0	TI	PMID[511963]
NPT947	Individual Protein	Carbonic anhydrase I	Homo sapiens	Ki	=	9310.0	nM	PMID[511965]
NPT955	Individual Protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	8870.0	nM	PMID[511965]
NPT948	Individual Protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	830.0	nM	PMID[511965]
NPT949	Individual Protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	810.0	nM	PMID[511965]

☑ 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 NPC241165 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	349
0.1-0.2	1453
0.2-0.3	3303
0.3-0.4	7663
0.4-0.5	11153
0.5-0.6	4091
0.6-0.7	6010
0.7-0.8	5344
0.8-0.85	2090
0.85-0.9	965
0.9-0.95	249
0.95-1	27

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC205797
1.0	High Similarity	NPC1220
1.0	High Similarity	NPC142563
1.0	High Similarity	NPC291551
1.0	High Similarity	NPC141822
0.9688	High Similarity	NPC469965
0.9618	High Similarity	NPC137262
0.9618	High Similarity	NPC35501
0.9618	High Similarity	NPC144512
0.9618	High Similarity	NPC47040
0.9618	High Similarity	NPC37428
0.9618	High Similarity	NPC278600
0.9603	High Similarity	NPC293642
0.9603	High Similarity	NPC139595
0.9603	High Similarity	NPC60704
0.9237	High Similarity	NPC469955
0.9237	High Similarity	NPC469952
0.9213	High Similarity	NPC202594
0.9213	High Similarity	NPC232692
0.9179	High Similarity	NPC279573
0.9091	High Similarity	NPC31849
0.9058	High Similarity	NPC469701
0.9055	High Similarity	NPC50720
0.9044	High Similarity	NPC152771
0.9044	High Similarity	NPC287286
0.9044	High Similarity	NPC195357
0.9037	High Similarity	NPC211110
0.9023	High Similarity	NPC131950
0.9015	High Similarity	NPC469956
0.8976	High Similarity	NPC150214
0.8971	High Similarity	NPC312881
0.8963	High Similarity	NPC184861
0.8963	High Similarity	NPC232246
0.8963	High Similarity	NPC225106
0.8963	High Similarity	NPC294456
0.8963	High Similarity	NPC281014
0.8963	High Similarity	NPC212124
0.8963	High Similarity	NPC153818
0.8939	High Similarity	NPC66430
0.8939	High Similarity	NPC37009
0.8923	High Similarity	NPC258567
0.8923	High Similarity	NPC224774
0.8923	High Similarity	NPC121740
0.8921	High Similarity	NPC106126
0.8921	High Similarity	NPC108994
0.8906	High Similarity	NPC143725
0.8897	High Similarity	NPC151946
0.8889	High Similarity	NPC78746
0.8889	High Similarity	NPC188380
0.8889	High Similarity	NPC224543
0.8889	High Similarity	NPC26954
0.8889	High Similarity	NPC38099
0.8881	High Similarity	NPC180716
0.8881	High Similarity	NPC326600
0.8881	High Similarity	NPC204353
0.8881	High Similarity	NPC62366
0.8881	High Similarity	NPC224475
0.8881	High Similarity	NPC213173
0.8881	High Similarity	NPC50896
0.8872	High Similarity	NPC194277
0.8864	High Similarity	NPC113098
0.8864	High Similarity	NPC32463
0.8855	High Similarity	NPC469453
0.8855	High Similarity	NPC185066
0.8837	High Similarity	NPC291899
0.8832	High Similarity	NPC71903
0.8824	High Similarity	NPC155963
0.8815	High Similarity	NPC472424
0.8815	High Similarity	NPC281241
0.8815	High Similarity	NPC472525
0.8815	High Similarity	NPC471909
0.8815	High Similarity	NPC86892
0.8815	High Similarity	NPC471625
0.8806	High Similarity	NPC318400
0.8806	High Similarity	NPC207002
0.8806	High Similarity	NPC167111
0.8806	High Similarity	NPC471910
0.8806	High Similarity	NPC83535
0.8806	High Similarity	NPC133956
0.8806	High Similarity	NPC296624
0.8797	High Similarity	NPC272650
0.8797	High Similarity	NPC267336
0.8797	High Similarity	NPC29734
0.8786	High Similarity	NPC43716
0.8786	High Similarity	NPC101255
0.8786	High Similarity	NPC475719
0.8779	High Similarity	NPC243688
0.8779	High Similarity	NPC289316
0.8768	High Similarity	NPC138149
0.8768	High Similarity	NPC170812
0.875	High Similarity	NPC128529
0.875	High Similarity	NPC149320
0.875	High Similarity	NPC160727
0.875	High Similarity	NPC471630
0.875	High Similarity	NPC55615
0.875	High Similarity	NPC476455
0.875	High Similarity	NPC177281
0.875	High Similarity	NPC283019
0.8741	High Similarity	NPC267412
0.8741	High Similarity	NPC287182
0.8741	High Similarity	NPC47163
0.8741	High Similarity	NPC195343
0.8741	High Similarity	NPC84894
0.8741	High Similarity	NPC319859
0.8741	High Similarity	NPC164269
0.8741	High Similarity	NPC127888
0.8741	High Similarity	NPC18804
0.8741	High Similarity	NPC198381
0.8741	High Similarity	NPC166672
0.8741	High Similarity	NPC74655
0.8741	High Similarity	NPC100986
0.8741	High Similarity	NPC260265
0.8705	High Similarity	NPC93640
0.8705	High Similarity	NPC20631
0.8702	High Similarity	NPC163248
0.8702	High Similarity	NPC471826
0.8692	High Similarity	NPC73413
0.8692	High Similarity	NPC27671
0.8692	High Similarity	NPC201667
0.8686	High Similarity	NPC131198
0.8667	High Similarity	NPC163557
0.8662	High Similarity	NPC87950
0.8662	High Similarity	NPC471764
0.8652	High Similarity	NPC85624
0.8647	High Similarity	NPC168710
0.8643	High Similarity	NPC201820
0.8636	High Similarity	NPC149796
0.8626	High Similarity	NPC471828
0.8626	High Similarity	NPC244495
0.8626	High Similarity	NPC471827
0.8626	High Similarity	NPC93219
0.8615	High Similarity	NPC273772
0.8615	High Similarity	NPC173350
0.8615	High Similarity	NPC290605
0.8615	High Similarity	NPC154176
0.8615	High Similarity	NPC472518
0.8615	High Similarity	NPC109675
0.8603	High Similarity	NPC98179
0.8603	High Similarity	NPC253574
0.8601	High Similarity	NPC285748
0.8601	High Similarity	NPC169510
0.8601	High Similarity	NPC177995
0.8601	High Similarity	NPC474108
0.8593	High Similarity	NPC14248
0.8582	High Similarity	NPC80170
0.8582	High Similarity	NPC471824
0.8571	High Similarity	NPC472519
0.8561	High Similarity	NPC276212
0.855	High Similarity	NPC111347
0.854	High Similarity	NPC33986
0.8538	High Similarity	NPC257188
0.8538	High Similarity	NPC13007
0.8538	High Similarity	NPC96286
0.8538	High Similarity	NPC248429
0.8531	High Similarity	NPC296377
0.8529	High Similarity	NPC469449
0.8529	High Similarity	NPC2363
0.8529	High Similarity	NPC222036
0.8529	High Similarity	NPC7526
0.8529	High Similarity	NPC77196
0.8521	High Similarity	NPC226722
0.8521	High Similarity	NPC295696
0.8519	High Similarity	NPC250727
0.8519	High Similarity	NPC244888
0.8519	High Similarity	NPC68205
0.8519	High Similarity	NPC118683
0.8519	High Similarity	NPC164804
0.8519	High Similarity	NPC293203
0.8519	High Similarity	NPC211413
0.8511	High Similarity	NPC229916
0.8511	High Similarity	NPC470555
0.8507	High Similarity	NPC134360
0.85	High Similarity	NPC279851
0.85	High Similarity	NPC472520
0.8489	Intermediate Similarity	NPC470209
0.8485	Intermediate Similarity	NPC102540
0.8485	Intermediate Similarity	NPC168259
0.8485	Intermediate Similarity	NPC285040
0.8485	Intermediate Similarity	NPC188022
0.8485	Intermediate Similarity	NPC17809
0.8485	Intermediate Similarity	NPC103420
0.8483	Intermediate Similarity	NPC164205
0.8483	Intermediate Similarity	NPC19238
0.8483	Intermediate Similarity	NPC104236
0.8483	Intermediate Similarity	NPC103116
0.8473	Intermediate Similarity	NPC315807
0.8467	Intermediate Similarity	NPC198154
0.8467	Intermediate Similarity	NPC307412
0.8467	Intermediate Similarity	NPC115335
0.8467	Intermediate Similarity	NPC55149
0.8467	Intermediate Similarity	NPC296915
0.8467	Intermediate Similarity	NPC97834
0.8467	Intermediate Similarity	NPC225696
0.8467	Intermediate Similarity	NPC223008
0.8462	Intermediate Similarity	NPC52247
0.8462	Intermediate Similarity	NPC187868
0.8456	Intermediate Similarity	NPC19157
0.8451	Intermediate Similarity	NPC471763
0.844	Intermediate Similarity	NPC221173
0.8433	Intermediate Similarity	NPC157212

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 NPC241165 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	311
0.1-0.2	930
0.2-0.3	1603
0.3-0.4	2518
0.4-0.5	2044
0.5-0.6	1127
0.6-0.7	414
0.7-0.8	149
0.8-0.85	37
0.85-0.9	13
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD5123	Clinical (unspecified phase)
1.0	High Similarity	NPD5124	Phase 1
0.8462	Intermediate Similarity	NPD422	Phase 1
0.8309	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD1652	Phase 2
0.8162	Intermediate Similarity	NPD4908	Phase 1
0.7914	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1610	Phase 2
0.7881	Intermediate Similarity	NPD7411	Suspended
0.7879	Intermediate Similarity	NPD1548	Phase 1
0.7868	Intermediate Similarity	NPD3225	Approved
0.781	Intermediate Similarity	NPD2797	Approved
0.7808	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7786	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7712	Intermediate Similarity	NPD6801	Discontinued
0.7708	Intermediate Similarity	NPD7033	Discontinued
0.7687	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD1653	Approved
0.7664	Intermediate Similarity	NPD4749	Approved
0.7662	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.766	Intermediate Similarity	NPD3268	Approved
0.7643	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7075	Discontinued
0.7619	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD5403	Approved
0.7613	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7603	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD4625	Phase 3
0.7582	Intermediate Similarity	NPD4380	Phase 2
0.7564	Intermediate Similarity	NPD7768	Phase 2
0.7552	Intermediate Similarity	NPD1613	Approved
0.7552	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1549	Phase 2
0.7548	Intermediate Similarity	NPD7819	Suspended
0.7535	Intermediate Similarity	NPD1296	Phase 2
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7517	Intermediate Similarity	NPD7097	Phase 1
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD5401	Approved
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7466	Intermediate Similarity	NPD3748	Approved
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD2424	Discontinued
0.7431	Intermediate Similarity	NPD4060	Phase 1
0.7424	Intermediate Similarity	NPD5535	Approved
0.7417	Intermediate Similarity	NPD7212	Phase 2
0.7417	Intermediate Similarity	NPD7213	Phase 3
0.7415	Intermediate Similarity	NPD2796	Approved
0.7405	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD1091	Approved
0.7372	Intermediate Similarity	NPD4626	Approved
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD2533	Approved
0.7368	Intermediate Similarity	NPD2534	Approved
0.7368	Intermediate Similarity	NPD2532	Approved
0.7351	Intermediate Similarity	NPD6666	Approved
0.7351	Intermediate Similarity	NPD6667	Approved
0.7346	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7342	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2861	Phase 2
0.7319	Intermediate Similarity	NPD3496	Discontinued
0.7317	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7315	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4140	Approved
0.7305	Intermediate Similarity	NPD3266	Approved
0.7305	Intermediate Similarity	NPD3267	Approved
0.7303	Intermediate Similarity	NPD6799	Approved
0.7299	Intermediate Similarity	NPD5691	Approved
0.7292	Intermediate Similarity	NPD6798	Discontinued
0.729	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5402	Approved
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD6674	Discontinued
0.726	Intermediate Similarity	NPD4340	Discontinued
0.7255	Intermediate Similarity	NPD7447	Phase 1
0.7254	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD7549	Discontinued
0.7234	Intermediate Similarity	NPD8651	Approved
0.7231	Intermediate Similarity	NPD3134	Approved
0.723	Intermediate Similarity	NPD4308	Phase 3
0.723	Intermediate Similarity	NPD1510	Phase 2
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD6651	Approved
0.7203	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD3749	Approved
0.7181	Intermediate Similarity	NPD6099	Approved
0.7181	Intermediate Similarity	NPD6100	Approved
0.7181	Intermediate Similarity	NPD1551	Phase 2
0.7161	Intermediate Similarity	NPD920	Approved
0.7154	Intermediate Similarity	NPD9697	Approved
0.7152	Intermediate Similarity	NPD1934	Approved
0.7152	Intermediate Similarity	NPD2800	Approved
0.7152	Intermediate Similarity	NPD1243	Approved
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7134	Intermediate Similarity	NPD6599	Discontinued
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD5763	Approved
0.7124	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD2684	Approved
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7107	Intermediate Similarity	NPD8455	Phase 2
0.7092	Intermediate Similarity	NPD9717	Approved
0.7083	Intermediate Similarity	NPD6559	Discontinued
0.7075	Intermediate Similarity	NPD1240	Approved
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7063	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD7985	Registered
0.7055	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7055	Intermediate Similarity	NPD6959	Discontinued
0.7047	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4536	Approved
0.7047	Intermediate Similarity	NPD4538	Approved
0.7045	Intermediate Similarity	NPD290	Approved
0.7045	Intermediate Similarity	NPD1358	Approved
0.7044	Intermediate Similarity	NPD37	Approved
0.7037	Intermediate Similarity	NPD7843	Approved
0.7034	Intermediate Similarity	NPD6832	Phase 2
0.7032	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6166	Phase 2
0.7029	Intermediate Similarity	NPD7644	Approved
0.7019	Intermediate Similarity	NPD4966	Approved
0.7019	Intermediate Similarity	NPD4967	Phase 2
0.7019	Intermediate Similarity	NPD4965	Approved
0.7013	Intermediate Similarity	NPD5058	Phase 3
0.7012	Intermediate Similarity	NPD7229	Phase 3
0.7007	Intermediate Similarity	NPD6671	Approved
0.7007	Intermediate Similarity	NPD6233	Phase 2
0.7006	Intermediate Similarity	NPD7054	Approved
0.7	Intermediate Similarity	NPD1778	Approved
0.6994	Remote Similarity	NPD5494	Approved
0.6993	Remote Similarity	NPD7466	Approved
0.6993	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6273	Approved
0.6987	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.698	Remote Similarity	NPD1607	Approved
0.6978	Remote Similarity	NPD1894	Discontinued
0.6964	Remote Similarity	NPD7472	Approved
0.6964	Remote Similarity	NPD7074	Phase 3
0.6959	Remote Similarity	NPD4307	Phase 2
0.6957	Remote Similarity	NPD4288	Approved
0.6957	Remote Similarity	NPD2415	Discontinued
0.6951	Remote Similarity	NPD7199	Phase 2
0.6944	Remote Similarity	NPD1203	Approved
0.6941	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3685	Discontinued
0.6923	Remote Similarity	NPD6797	Phase 2
0.6923	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD846	Approved
0.6923	Remote Similarity	NPD940	Approved
0.6909	Remote Similarity	NPD5710	Approved
0.6909	Remote Similarity	NPD5711	Approved
0.6908	Remote Similarity	NPD7266	Discontinued
0.6897	Remote Similarity	NPD3691	Phase 2
0.6897	Remote Similarity	NPD3690	Phase 2
0.6894	Remote Similarity	NPD2801	Approved
0.6887	Remote Similarity	NPD5588	Approved
0.6887	Remote Similarity	NPD5960	Phase 3
0.6884	Remote Similarity	NPD7157	Approved
0.6883	Remote Similarity	NPD7003	Approved
0.6882	Remote Similarity	NPD7251	Discontinued
0.6871	Remote Similarity	NPD7095	Approved
0.6859	Remote Similarity	NPD1511	Approved
0.6859	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD8127	Discontinued
0.6846	Remote Similarity	NPD2203	Discontinued
0.6845	Remote Similarity	NPD7228	Approved
0.6845	Remote Similarity	NPD3818	Discontinued
0.6842	Remote Similarity	NPD7808	Phase 3
0.6842	Remote Similarity	NPD4477	Approved
0.6842	Remote Similarity	NPD4476	Approved
0.6842	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD7340	Approved
0.6832	Remote Similarity	NPD4433	Discontinued
0.6831	Remote Similarity	NPD3847	Discontinued
0.6829	Remote Similarity	NPD6234	Discontinued
0.6829	Remote Similarity	NPD919	Approved
0.6828	Remote Similarity	NPD6362	Approved
0.6824	Remote Similarity	NPD5953	Discontinued
0.6824	Remote Similarity	NPD1048	Approved
0.6821	Remote Similarity	NPD2200	Suspended
0.6813	Remote Similarity	NPD6502	Phase 2
0.6807	Remote Similarity	NPD6232	Discontinued
0.6806	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7286	Phase 2

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