NPASS Compound

Structure

NPC469965 OpenBabel07101719252D 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 1 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 1 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 1 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 1 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 1 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 3 1 6 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 1 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:	372.19
Volume:	385.611
LogP:	5.576
LogD:	4.099
LogS:	-4.098
# 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:	0.796
Synthetic Accessibility Score:	4.09
Fsp3:	0.591
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:	2.1847810785402544e-05
Pgp-inhibitor:	0.785
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.082
Plasma Protein Binding (PPB):	93.56136322021484%
Volume Distribution (VD):	1.659
Pgp-substrate:	6.4785943031311035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.318
CYP1A2-substrate:	0.932
CYP2C19-inhibitor:	0.369
CYP2C19-substrate:	0.831
CYP2C9-inhibitor:	0.47
CYP2C9-substrate:	0.915
CYP2D6-inhibitor:	0.36
CYP2D6-substrate:	0.468
CYP3A4-inhibitor:	0.296
CYP3A4-substrate:	0.268

ADMET: Excretion

Clearance (CL):	8.165
Half-life (T1/2):	0.161

ADMET: Toxicity

hERG Blockers:	0.022
Human Hepatotoxicity (H-HT):	0.725
Drug-inuced Liver Injury (DILI):	0.766
AMES Toxicity:	0.08
Rat Oral Acute Toxicity:	0.775
Maximum Recommended Daily Dose:	0.633
Skin Sensitization:	0.344
Carcinogencity:	0.486
Eye Corrosion:	0.003
Eye Irritation:	0.015
Respiratory Toxicity:	0.104

Download Data

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

Natural Product: NPC469965

Natural Product ID:	NPC469965
*Common Name:**	7,8-Dihydrocalanolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YPUTYHJWWMYIGF-PZROIBLQSA-N
Standard InCHI:	InChI=1S/C22H28O5/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/h10-12,18,24H,6-9H2,1-5H3/t11-,12-,18-/m0/s1
SMILES:	CCCC1=CC(=O)OC2=C1C3=C(CCC(O3)(C)C)C4=C2C(C(C(O4)C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL138469
PubChem CID:	65061
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	2
IC50	1
Others	2

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	1
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT315	Cell Line	CEM-SS	Homo sapiens	EC50	=	200.0	nM	PMID[449009]
NPT315	Cell Line	CEM-SS	Homo sapiens	IC50	=	8200.0	nM	PMID[449009]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	TI	=	41.0	n.a.	PMID[449009]
NPT24	Organism	Human immunodeficiency virus 1	Human immunodeficiency virus 1	EC50	=	100.0	nM	PMID[449010]
NPT27	Others	Unspecified		TI	=	99.8	n.a.	PMID[449010]

☑ 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 NPC469965 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	346
0.1-0.2	1470
0.2-0.3	3303
0.3-0.4	7720
0.4-0.5	11270
0.5-0.6	4133
0.6-0.7	5927
0.7-0.8	5332
0.8-0.85	2025
0.85-0.9	940
0.9-0.95	206
0.95-1	25

Similarity Score	Similarity Level	Natural Product ID
0.9688	High Similarity	NPC142563
0.9688	High Similarity	NPC141822
0.9688	High Similarity	NPC205797
0.9688	High Similarity	NPC1220
0.9688	High Similarity	NPC291551
0.9688	High Similarity	NPC241165
0.9323	High Similarity	NPC47040
0.9323	High Similarity	NPC278600
0.9323	High Similarity	NPC37428
0.9323	High Similarity	NPC144512
0.9323	High Similarity	NPC35501
0.9323	High Similarity	NPC137262
0.9297	High Similarity	NPC139595
0.9297	High Similarity	NPC60704
0.9297	High Similarity	NPC293642
0.9197	High Similarity	NPC469701
0.9179	High Similarity	NPC279573
0.9091	High Similarity	NPC31849
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
0.8971	High Similarity	NPC312881
0.8963	High Similarity	NPC294456
0.8963	High Similarity	NPC184861
0.8963	High Similarity	NPC153818
0.8963	High Similarity	NPC225106
0.8963	High Similarity	NPC281014
0.8963	High Similarity	NPC212124
0.8963	High Similarity	NPC232246
0.8947	High Similarity	NPC469952
0.8947	High Similarity	NPC469955
0.8921	High Similarity	NPC108994
0.8921	High Similarity	NPC106126
0.8915	High Similarity	NPC232692
0.8915	High Similarity	NPC202594
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	NPC224475
0.8881	High Similarity	NPC180716
0.8881	High Similarity	NPC326600
0.8881	High Similarity	NPC204353
0.8881	High Similarity	NPC62366
0.8881	High Similarity	NPC213173
0.8881	High Similarity	NPC50896
0.8872	High Similarity	NPC194277
0.8855	High Similarity	NPC185066
0.8824	High Similarity	NPC155963
0.8815	High Similarity	NPC472525
0.8815	High Similarity	NPC472424
0.8815	High Similarity	NPC281241
0.8815	High Similarity	NPC471909
0.8815	High Similarity	NPC86892
0.8815	High Similarity	NPC471625
0.8806	High Similarity	NPC167111
0.8806	High Similarity	NPC318400
0.8806	High Similarity	NPC207002
0.8806	High Similarity	NPC471910
0.8806	High Similarity	NPC133956
0.8806	High Similarity	NPC296624
0.8797	High Similarity	NPC37009
0.8797	High Similarity	NPC66430
0.8794	High Similarity	NPC87950
0.8794	High Similarity	NPC471764
0.8786	High Similarity	NPC475719
0.8786	High Similarity	NPC43716
0.8786	High Similarity	NPC101255
0.8779	High Similarity	NPC121740
0.8779	High Similarity	NPC258567
0.8779	High Similarity	NPC224774
0.8768	High Similarity	NPC138149
0.876	High Similarity	NPC50720
0.875	High Similarity	NPC149320
0.875	High Similarity	NPC128529
0.875	High Similarity	NPC160727
0.875	High Similarity	NPC55615
0.875	High Similarity	NPC476455
0.875	High Similarity	NPC177281
0.875	High Similarity	NPC283019
0.875	High Similarity	NPC471630
0.8741	High Similarity	NPC267412
0.8741	High Similarity	NPC287182
0.8741	High Similarity	NPC195343
0.8741	High Similarity	NPC84894
0.8741	High Similarity	NPC319859
0.8741	High Similarity	NPC164269
0.8741	High Similarity	NPC47163
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
0.8731	High Similarity	NPC469956
0.8722	High Similarity	NPC113098
0.8722	High Similarity	NPC32463
0.8712	High Similarity	NPC469453
0.8705	High Similarity	NPC93640
0.8705	High Similarity	NPC20631
0.8702	High Similarity	NPC471826
0.8686	High Similarity	NPC131198
0.8682	High Similarity	NPC150214
0.8667	High Similarity	NPC83535
0.8667	High Similarity	NPC163557
0.8657	High Similarity	NPC267336
0.8657	High Similarity	NPC29734
0.8657	High Similarity	NPC272650
0.8652	High Similarity	NPC85624
0.8647	High Similarity	NPC168710
0.8636	High Similarity	NPC243688
0.8636	High Similarity	NPC289316
0.8626	High Similarity	NPC471828
0.8626	High Similarity	NPC471827
0.8615	High Similarity	NPC143725
0.8603	High Similarity	NPC98179
0.8603	High Similarity	NPC253574
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
0.8561	High Similarity	NPC71903
0.8561	High Similarity	NPC163248
0.855	High Similarity	NPC27671
0.855	High Similarity	NPC201667
0.855	High Similarity	NPC291899
0.855	High Similarity	NPC111347
0.855	High Similarity	NPC73413
0.854	High Similarity	NPC33986
0.8531	High Similarity	NPC296377
0.8529	High Similarity	NPC222036
0.8529	High Similarity	NPC7526
0.8521	High Similarity	NPC474939
0.8521	High Similarity	NPC96216
0.8521	High Similarity	NPC470909
0.8521	High Similarity	NPC295696
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
0.85	High Similarity	NPC279851
0.85	High Similarity	NPC472520
0.85	High Similarity	NPC170812
0.8496	Intermediate Similarity	NPC149796
0.8489	Intermediate Similarity	NPC470209
0.8485	Intermediate Similarity	NPC244495
0.8485	Intermediate Similarity	NPC93219
0.8483	Intermediate Similarity	NPC103116
0.8473	Intermediate Similarity	NPC472518
0.8473	Intermediate Similarity	NPC109675
0.8473	Intermediate Similarity	NPC273772
0.8472	Intermediate Similarity	NPC285748
0.8467	Intermediate Similarity	NPC97834
0.8467	Intermediate Similarity	NPC198154
0.8467	Intermediate Similarity	NPC307412
0.8467	Intermediate Similarity	NPC115335
0.8467	Intermediate Similarity	NPC225696
0.8467	Intermediate Similarity	NPC55149
0.8467	Intermediate Similarity	NPC296915
0.8467	Intermediate Similarity	NPC223008
0.8462	Intermediate Similarity	NPC470554
0.8462	Intermediate Similarity	NPC288910
0.8462	Intermediate Similarity	NPC471608
0.8462	Intermediate Similarity	NPC118059
0.8462	Intermediate Similarity	NPC187868
0.8462	Intermediate Similarity	NPC133060
0.8451	Intermediate Similarity	NPC470556
0.8451	Intermediate Similarity	NPC294432
0.8451	Intermediate Similarity	NPC471763
0.8433	Intermediate Similarity	NPC274717
0.8433	Intermediate Similarity	NPC199204
0.8433	Intermediate Similarity	NPC472519
0.8421	Intermediate Similarity	NPC188327
0.8421	Intermediate Similarity	NPC234109
0.8421	Intermediate Similarity	NPC276212
0.8417	Intermediate Similarity	NPC306365
0.8406	Intermediate Similarity	NPC469675
0.8403	Intermediate Similarity	NPC470910
0.8397	Intermediate Similarity	NPC96286
0.8397	Intermediate Similarity	NPC248429
0.8394	Intermediate Similarity	NPC77196
0.8394	Intermediate Similarity	NPC2363
0.8394	Intermediate Similarity	NPC469449
0.8392	Intermediate Similarity	NPC226722
0.8392	Intermediate Similarity	NPC470553
0.8392	Intermediate Similarity	NPC33653
0.8392	Intermediate Similarity	NPC307895
0.8392	Intermediate Similarity	NPC184738
0.8382	Intermediate Similarity	NPC250727
0.838	Intermediate Similarity	NPC201820

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 NPC469965 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	313
0.1-0.2	943
0.2-0.3	1680
0.3-0.4	2511
0.4-0.5	2027
0.5-0.6	1099
0.6-0.7	384
0.7-0.8	145
0.8-0.85	34
0.85-0.9	11
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9688	High Similarity	NPD5124	Phase 1
0.9688	High Similarity	NPD5123	Clinical (unspecified phase)
0.8321	Intermediate Similarity	NPD422	Phase 1
0.8309	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.8162	Intermediate Similarity	NPD4908	Phase 1
0.8112	Intermediate Similarity	NPD1652	Phase 2
0.7931	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7914	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.791	Intermediate Similarity	NPD1610	Phase 2
0.7794	Intermediate Similarity	NPD4749	Approved
0.7786	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7411	Suspended
0.7744	Intermediate Similarity	NPD1548	Phase 1
0.7687	Intermediate Similarity	NPD3750	Approved
0.7682	Intermediate Similarity	NPD1653	Approved
0.7681	Intermediate Similarity	NPD2797	Approved
0.7662	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7628	Intermediate Similarity	NPD7075	Discontinued
0.7613	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3225	Approved
0.76	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.76	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7597	Intermediate Similarity	NPD6801	Discontinued
0.7589	Intermediate Similarity	NPD4625	Phase 3
0.7586	Intermediate Similarity	NPD7033	Discontinued
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)
0.7548	Intermediate Similarity	NPD7819	Suspended
0.7535	Intermediate Similarity	NPD3268	Approved
0.7531	Intermediate Similarity	NPD5844	Phase 1
0.7518	Intermediate Similarity	NPD1008	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6002	Phase 3
0.7483	Intermediate Similarity	NPD6005	Phase 3
0.7483	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD2532	Approved
0.7483	Intermediate Similarity	NPD2533	Approved
0.7483	Intermediate Similarity	NPD2534	Approved
0.7483	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7483	Intermediate Similarity	NPD6004	Phase 3
0.7466	Intermediate Similarity	NPD3748	Approved
0.7452	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7432	Intermediate Similarity	NPD1549	Phase 2
0.7432	Intermediate Similarity	NPD2424	Discontinued
0.7432	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7431	Intermediate Similarity	NPD4060	Phase 1
0.7423	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD2796	Approved
0.7413	Intermediate Similarity	NPD1296	Phase 2
0.7405	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD7097	Phase 1
0.7386	Intermediate Similarity	NPD5403	Approved
0.7383	Intermediate Similarity	NPD6674	Discontinued
0.7376	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4626	Approved
0.7368	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6666	Approved
0.7351	Intermediate Similarity	NPD6667	Approved
0.7346	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7324	Intermediate Similarity	NPD2861	Phase 2
0.7319	Intermediate Similarity	NPD3496	Discontinued
0.731	Intermediate Similarity	NPD4140	Approved
0.7303	Intermediate Similarity	NPD7213	Phase 3
0.7303	Intermediate Similarity	NPD7212	Phase 2
0.7299	Intermediate Similarity	NPD5691	Approved
0.7297	Intermediate Similarity	NPD6100	Approved
0.7297	Intermediate Similarity	NPD6099	Approved
0.7293	Intermediate Similarity	NPD5535	Approved
0.729	Intermediate Similarity	NPD8158	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2800	Approved
0.7267	Intermediate Similarity	NPD6959	Discontinued
0.7267	Intermediate Similarity	NPD1243	Approved
0.7266	Intermediate Similarity	NPD1091	Approved
0.7255	Intermediate Similarity	NPD5401	Approved
0.7255	Intermediate Similarity	NPD7447	Phase 1
0.7246	Intermediate Similarity	NPD7549	Discontinued
0.7234	Intermediate Similarity	NPD8651	Approved
0.723	Intermediate Similarity	NPD1510	Phase 2
0.723	Intermediate Similarity	NPD4308	Phase 3
0.7222	Intermediate Similarity	NPD3027	Phase 3
0.7219	Intermediate Similarity	NPD4628	Phase 3
0.7219	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7215	Intermediate Similarity	NPD8455	Phase 2
0.7211	Intermediate Similarity	NPD6651	Approved
0.719	Intermediate Similarity	NPD6799	Approved
0.7188	Intermediate Similarity	NPD3749	Approved
0.7183	Intermediate Similarity	NPD3267	Approved
0.7183	Intermediate Similarity	NPD3266	Approved
0.7181	Intermediate Similarity	NPD1551	Phase 2
0.7172	Intermediate Similarity	NPD7985	Registered
0.7172	Intermediate Similarity	NPD6798	Discontinued
0.7172	Intermediate Similarity	NPD1699	Clinical (unspecified phase)
0.717	Intermediate Similarity	NPD5402	Approved
0.7161	Intermediate Similarity	NPD920	Approved
0.7153	Intermediate Similarity	NPD7644	Approved
0.7152	Intermediate Similarity	NPD37	Approved
0.7152	Intermediate Similarity	NPD1934	Approved
0.7152	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6355	Discontinued
0.7143	Intermediate Similarity	NPD4340	Discontinued
0.7134	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD6166	Phase 2
0.7133	Intermediate Similarity	NPD5762	Approved
0.7133	Intermediate Similarity	NPD5763	Approved
0.7126	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7125	Intermediate Similarity	NPD4967	Phase 2
0.7125	Intermediate Similarity	NPD4966	Approved
0.7125	Intermediate Similarity	NPD4965	Approved
0.7124	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7114	Intermediate Similarity	NPD2799	Discontinued
0.7108	Intermediate Similarity	NPD7054	Approved
0.7105	Intermediate Similarity	NPD7982	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD3134	Approved
0.7099	Intermediate Similarity	NPD5494	Approved
0.7083	Intermediate Similarity	NPD6559	Discontinued
0.7067	Intermediate Similarity	NPD2935	Discontinued
0.7066	Intermediate Similarity	NPD7074	Phase 3
0.7066	Intermediate Similarity	NPD7472	Approved
0.7063	Intermediate Similarity	NPD3817	Phase 2
0.7055	Intermediate Similarity	NPD2313	Discontinued
0.7048	Intermediate Similarity	NPD7228	Approved
0.7047	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7047	Intermediate Similarity	NPD4536	Approved
0.7047	Intermediate Similarity	NPD4538	Approved
0.7032	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7025	Intermediate Similarity	NPD6599	Discontinued
0.7024	Intermediate Similarity	NPD6797	Phase 2
0.7023	Intermediate Similarity	NPD9697	Approved
0.702	Intermediate Similarity	NPD7266	Discontinued
0.7013	Intermediate Similarity	NPD5058	Phase 3
0.7012	Intermediate Similarity	NPD5710	Approved
0.7012	Intermediate Similarity	NPD5711	Approved
0.7012	Intermediate Similarity	NPD7229	Phase 3
0.7007	Intermediate Similarity	NPD6671	Approved
0.7	Intermediate Similarity	NPD1778	Approved
0.7	Intermediate Similarity	NPD1465	Phase 2
0.6993	Remote Similarity	NPD7466	Approved
0.6992	Remote Similarity	NPD2684	Approved
0.6987	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD6273	Approved
0.6982	Remote Similarity	NPD7251	Discontinued
0.6972	Remote Similarity	NPD9717	Approved
0.6968	Remote Similarity	NPD7837	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD4307	Phase 2
0.6959	Remote Similarity	NPD1240	Approved
0.6957	Remote Similarity	NPD4288	Approved
0.6957	Remote Similarity	NPD7340	Approved
0.6957	Remote Similarity	NPD2415	Discontinued
0.6951	Remote Similarity	NPD7199	Phase 2
0.6941	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD7808	Phase 3
0.6933	Remote Similarity	NPD6234	Discontinued
0.6918	Remote Similarity	NPD6832	Phase 2
0.6917	Remote Similarity	NPD290	Approved
0.6917	Remote Similarity	NPD1358	Approved
0.6912	Remote Similarity	NPD7843	Approved
0.6897	Remote Similarity	NPD3691	Phase 2
0.6897	Remote Similarity	NPD3690	Phase 2
0.6894	Remote Similarity	NPD2801	Approved
0.6892	Remote Similarity	NPD6233	Phase 2
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
0.6871	Remote Similarity	NPD7095	Approved
0.6867	Remote Similarity	NPD1607	Approved
0.6861	Remote Similarity	NPD1398	Phase 1
0.6859	Remote Similarity	NPD1511	Approved
0.6857	Remote Similarity	NPD1894	Discontinued
0.6853	Remote Similarity	NPD1608	Approved
0.6848	Remote Similarity	NPD8127	Discontinued
0.6845	Remote Similarity	NPD3818	Discontinued
0.6842	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD4477	Approved
0.6842	Remote Similarity	NPD4476	Approved
0.6832	Remote Similarity	NPD4433	Discontinued
0.6829	Remote Similarity	NPD919	Approved
0.6828	Remote Similarity	NPD1203	Approved
0.6824	Remote Similarity	NPD5953	Discontinued
0.6821	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD2200	Suspended
0.6807	Remote Similarity	NPD6232	Discontinued
0.6806	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3685	Discontinued
0.6797	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD2346	Discontinued
0.6794	Remote Similarity	NPD846	Approved
0.6794	Remote Similarity	NPD940	Approved
0.6786	Remote Similarity	NPD7473	Discontinued
0.6784	Remote Similarity	NPD7240	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