NPASS Compound

Structure

NPC475994 OpenBabel07101718282D 21 22 0 0 1 0 0 0 0 0999 V2000 2.4009 3.0476 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6030 -1.4389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2935 -1.2935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7670 0.4735 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8415 -0.2255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6953 0.5472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3285 -0.8215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2495 2.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4573 1.7068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9563 1.7068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4136 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1641 -1.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1641 2.1641 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9563 -0.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9147 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4136 0.9147 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.4573 -0.7921 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2495 -1.2495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2971 1.1514 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0127 -2.1330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 2 14 1 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 7 17 2 0 0 0 0 8 9 1 0 0 0 0 8 13 1 0 0 0 0 9 15 1 0 0 0 0 10 13 1 0 0 0 0 10 16 1 0 0 0 0 11 14 2 0 0 0 0 11 16 1 0 0 0 0 12 14 1 0 0 0 0 12 18 1 0 0 0 0 15 6 1 1 0 0 0 15 19 1 0 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 21 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	288.21
Volume:	327.102
LogP:	3.766
LogD:	3.267
LogS:	-4.026
# Rotatable Bonds:	0
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.678
Synthetic Accessibility Score:	5.597
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.569
MDCK Permeability:	3.0973798857303336e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.314
30% Bioavailability (F30%):	0.065

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.905
Plasma Protein Binding (PPB):	89.61002349853516%
Volume Distribution (VD):	1.395
Pgp-substrate:	10.733795166015625%

ADMET: Metabolism

CYP1A2-inhibitor:	0.04
CYP1A2-substrate:	0.577
CYP2C19-inhibitor:	0.289
CYP2C19-substrate:	0.866
CYP2C9-inhibitor:	0.198
CYP2C9-substrate:	0.779
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.751
CYP3A4-inhibitor:	0.236
CYP3A4-substrate:	0.397

ADMET: Excretion

Clearance (CL):	7.505
Half-life (T1/2):	0.305

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.069
Drug-inuced Liver Injury (DILI):	0.02
AMES Toxicity:	0.011
Rat Oral Acute Toxicity:	0.013
Maximum Recommended Daily Dose:	0.843
Skin Sensitization:	0.227
Carcinogencity:	0.09
Eye Corrosion:	0.013
Eye Irritation:	0.598
Respiratory Toxicity:	0.967

Download Data

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

Natural Product: NPC475994

Natural Product ID:	NPC475994
*Common Name:**	Cesputularin E
IUPAC Name:	(1S,7E)-6-hydroxy-8,15,15-trimethyl-4-methylidenebicyclo[9.3.1]pentadeca-7,11-dien-10-one
Synonyms:	Cesputularin E
Standard InCHIKey:	JWAJDLYSFBHBSW-ANCIEEHGSA-N
Standard InCHI:	InChI=1S/C19H28O2/c1-13-8-9-15-6-5-7-17(19(15,3)4)18(21)12-14(2)11-16(20)10-13/h7,11,15-16,20H,1,5-6,8-10,12H2,2-4H3/b14-11+/t15-,16?/m0/s1
SMILES:	CC1=CC(CC(=C)CCC2CCC=C(C2(C)C)C(=O)C1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL520672
PubChem CID:	10062665
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001661] Secondary alcohols

*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
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[12398538]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[19061391]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	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
ED50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	ED50	=	0.034	ug ml-1	PMID[558688]
NPT168	Cell Line	P388	Mus musculus	ED50	=	4.66	ug ml-1	PMID[558688]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	17.1	ug ml-1	PMID[558688]

☑ 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 NPC475994 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	174
0.1-0.2	1117
0.2-0.3	5311
0.3-0.4	14204
0.4-0.5	10543
0.5-0.6	6170
0.6-0.7	4118
0.7-0.8	938
0.8-0.85	95
0.85-0.9	22
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9079	High Similarity	NPC19900
0.9079	High Similarity	NPC308038
0.9041	High Similarity	NPC186042
0.9	High Similarity	NPC472974
0.8974	High Similarity	NPC38796
0.8974	High Similarity	NPC158411
0.8947	High Similarity	NPC62336
0.8933	High Similarity	NPC263582
0.8933	High Similarity	NPC470525
0.8919	High Similarity	NPC215050
0.8875	High Similarity	NPC179006
0.8875	High Similarity	NPC474853
0.8875	High Similarity	NPC476426
0.8816	High Similarity	NPC74995
0.88	High Similarity	NPC114236
0.8765	High Similarity	NPC194417
0.875	High Similarity	NPC476412
0.8734	High Similarity	NPC93590
0.8718	High Similarity	NPC45495
0.8608	High Similarity	NPC6663
0.8608	High Similarity	NPC136150
0.859	High Similarity	NPC152061
0.859	High Similarity	NPC7232
0.859	High Similarity	NPC281138
0.8571	High Similarity	NPC471061
0.8537	High Similarity	NPC472985
0.8537	High Similarity	NPC472986
0.8493	Intermediate Similarity	NPC117804
0.8481	Intermediate Similarity	NPC148685
0.8481	Intermediate Similarity	NPC271104
0.8481	Intermediate Similarity	NPC2482
0.8481	Intermediate Similarity	NPC157895
0.8481	Intermediate Similarity	NPC172013
0.8481	Intermediate Similarity	NPC104120
0.8462	Intermediate Similarity	NPC297996
0.8452	Intermediate Similarity	NPC472983
0.8452	Intermediate Similarity	NPC472973
0.8452	Intermediate Similarity	NPC123912
0.8442	Intermediate Similarity	NPC469646
0.8434	Intermediate Similarity	NPC312561
0.84	Intermediate Similarity	NPC95863
0.8395	Intermediate Similarity	NPC105173
0.8375	Intermediate Similarity	NPC116797
0.8375	Intermediate Similarity	NPC121984
0.8372	Intermediate Similarity	NPC474736
0.8372	Intermediate Similarity	NPC109305
0.8353	Intermediate Similarity	NPC48010
0.8333	Intermediate Similarity	NPC474854
0.8333	Intermediate Similarity	NPC197659
0.8333	Intermediate Similarity	NPC97377
0.8333	Intermediate Similarity	NPC203403
0.8313	Intermediate Similarity	NPC470955
0.8312	Intermediate Similarity	NPC474885
0.8312	Intermediate Similarity	NPC474011
0.8293	Intermediate Similarity	NPC7927
0.8293	Intermediate Similarity	NPC230527
0.8293	Intermediate Similarity	NPC472326
0.8289	Intermediate Similarity	NPC323437
0.8289	Intermediate Similarity	NPC29542
0.8289	Intermediate Similarity	NPC201562
0.8289	Intermediate Similarity	NPC275098
0.8276	Intermediate Similarity	NPC472977
0.8276	Intermediate Similarity	NPC472976
0.8272	Intermediate Similarity	NPC103486
0.8256	Intermediate Similarity	NPC472978
0.825	Intermediate Similarity	NPC471514
0.825	Intermediate Similarity	NPC306095
0.825	Intermediate Similarity	NPC472478
0.8235	Intermediate Similarity	NPC309603
0.8235	Intermediate Similarity	NPC473999
0.8228	Intermediate Similarity	NPC471409
0.8228	Intermediate Similarity	NPC275494
0.8228	Intermediate Similarity	NPC231739
0.8228	Intermediate Similarity	NPC478122
0.8214	Intermediate Similarity	NPC287079
0.8193	Intermediate Similarity	NPC471224
0.8193	Intermediate Similarity	NPC474083
0.8193	Intermediate Similarity	NPC274724
0.8193	Intermediate Similarity	NPC255174
0.8193	Intermediate Similarity	NPC15807
0.8171	Intermediate Similarity	NPC169941
0.8171	Intermediate Similarity	NPC251475
0.8171	Intermediate Similarity	NPC49019
0.8171	Intermediate Similarity	NPC470165
0.8158	Intermediate Similarity	NPC474884
0.8148	Intermediate Similarity	NPC470298
0.8148	Intermediate Similarity	NPC14151
0.814	Intermediate Similarity	NPC281942
0.814	Intermediate Similarity	NPC232426
0.8133	Intermediate Similarity	NPC10758
0.8133	Intermediate Similarity	NPC250928
0.8125	Intermediate Similarity	NPC476177
0.8125	Intermediate Similarity	NPC472490
0.8118	Intermediate Similarity	NPC104560
0.8108	Intermediate Similarity	NPC269985
0.8108	Intermediate Similarity	NPC114651
0.8108	Intermediate Similarity	NPC106613
0.8108	Intermediate Similarity	NPC96962
0.8101	Intermediate Similarity	NPC266193
0.8101	Intermediate Similarity	NPC276769
0.8101	Intermediate Similarity	NPC325946
0.8101	Intermediate Similarity	NPC257666
0.8101	Intermediate Similarity	NPC211279
0.8101	Intermediate Similarity	NPC476007
0.8101	Intermediate Similarity	NPC86917
0.8095	Intermediate Similarity	NPC474778
0.8095	Intermediate Similarity	NPC145879
0.8095	Intermediate Similarity	NPC473226
0.8095	Intermediate Similarity	NPC474732
0.8095	Intermediate Similarity	NPC222613
0.8095	Intermediate Similarity	NPC94666
0.8095	Intermediate Similarity	NPC118648
0.8095	Intermediate Similarity	NPC31564
0.8095	Intermediate Similarity	NPC474733
0.8095	Intermediate Similarity	NPC82979
0.8095	Intermediate Similarity	NPC475022
0.809	Intermediate Similarity	NPC117133
0.8072	Intermediate Similarity	NPC85774
0.8072	Intermediate Similarity	NPC58841
0.8072	Intermediate Similarity	NPC329043
0.8072	Intermediate Similarity	NPC161423
0.8072	Intermediate Similarity	NPC227132
0.8072	Intermediate Similarity	NPC227064
0.8072	Intermediate Similarity	NPC40687
0.8072	Intermediate Similarity	NPC321187
0.8072	Intermediate Similarity	NPC473246
0.8072	Intermediate Similarity	NPC214043
0.8068	Intermediate Similarity	NPC53685
0.8052	Intermediate Similarity	NPC247586
0.8049	Intermediate Similarity	NPC151519
0.8049	Intermediate Similarity	NPC279186
0.8049	Intermediate Similarity	NPC212083
0.8046	Intermediate Similarity	NPC475806
0.8046	Intermediate Similarity	NPC141831
0.8046	Intermediate Similarity	NPC472975
0.8046	Intermediate Similarity	NPC473998
0.8046	Intermediate Similarity	NPC116726
0.8026	Intermediate Similarity	NPC173321
0.8026	Intermediate Similarity	NPC286154
0.8025	Intermediate Similarity	NPC472301
0.8025	Intermediate Similarity	NPC108955
0.8023	Intermediate Similarity	NPC214387
0.8023	Intermediate Similarity	NPC473100
0.8023	Intermediate Similarity	NPC5509
0.8023	Intermediate Similarity	NPC119416
0.8	Intermediate Similarity	NPC58063
0.8	Intermediate Similarity	NPC74410
0.8	Intermediate Similarity	NPC475740
0.8	Intermediate Similarity	NPC470523
0.8	Intermediate Similarity	NPC198240
0.8	Intermediate Similarity	NPC220930
0.8	Intermediate Similarity	NPC239098
0.8	Intermediate Similarity	NPC272039
0.8	Intermediate Similarity	NPC192006
0.8	Intermediate Similarity	NPC178852
0.8	Intermediate Similarity	NPC189485
0.7978	Intermediate Similarity	NPC472932
0.7976	Intermediate Similarity	NPC470574
0.7976	Intermediate Similarity	NPC32037
0.7976	Intermediate Similarity	NPC70685
0.7976	Intermediate Similarity	NPC469948
0.7976	Intermediate Similarity	NPC79573
0.7976	Intermediate Similarity	NPC36350
0.7975	Intermediate Similarity	NPC180886
0.7975	Intermediate Similarity	NPC250621
0.7975	Intermediate Similarity	NPC151622
0.7975	Intermediate Similarity	NPC7629
0.7975	Intermediate Similarity	NPC472305
0.7955	Intermediate Similarity	NPC115021
0.7955	Intermediate Similarity	NPC69454
0.7955	Intermediate Similarity	NPC472930
0.7952	Intermediate Similarity	NPC297398
0.7952	Intermediate Similarity	NPC193198
0.7952	Intermediate Similarity	NPC64600
0.7931	Intermediate Similarity	NPC134321
0.7931	Intermediate Similarity	NPC473099
0.7931	Intermediate Similarity	NPC230332
0.7931	Intermediate Similarity	NPC69622
0.7931	Intermediate Similarity	NPC477149
0.7931	Intermediate Similarity	NPC477147
0.7927	Intermediate Similarity	NPC90055
0.7927	Intermediate Similarity	NPC55869
0.7927	Intermediate Similarity	NPC473420
0.7922	Intermediate Similarity	NPC84790
0.7912	Intermediate Similarity	NPC478056
0.7912	Intermediate Similarity	NPC235464
0.7912	Intermediate Similarity	NPC166745
0.7912	Intermediate Similarity	NPC197386
0.7907	Intermediate Similarity	NPC206060
0.7907	Intermediate Similarity	NPC53454
0.7907	Intermediate Similarity	NPC471791
0.7907	Intermediate Similarity	NPC473229
0.7907	Intermediate Similarity	NPC249889
0.7907	Intermediate Similarity	NPC158778
0.7907	Intermediate Similarity	NPC471793
0.7907	Intermediate Similarity	NPC470524
0.7907	Intermediate Similarity	NPC193843
0.7907	Intermediate Similarity	NPC471722
0.7901	Intermediate Similarity	NPC170394
0.7901	Intermediate Similarity	NPC229204

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 NPC475994 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	161
0.1-0.2	1723
0.2-0.3	3884
0.3-0.4	2287
0.4-0.5	672
0.5-0.6	250
0.6-0.7	146
0.7-0.8	27
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8072	Intermediate Similarity	NPD3666	Approved
0.8072	Intermediate Similarity	NPD3133	Approved
0.8072	Intermediate Similarity	NPD3665	Phase 1
0.8049	Intermediate Similarity	NPD3667	Approved
0.8025	Intermediate Similarity	NPD4695	Discontinued
0.7882	Intermediate Similarity	NPD3618	Phase 1
0.7882	Intermediate Similarity	NPD5279	Phase 3
0.7857	Intermediate Similarity	NPD4786	Approved
0.7765	Intermediate Similarity	NPD1696	Phase 3
0.7674	Intermediate Similarity	NPD4519	Discontinued
0.7674	Intermediate Similarity	NPD4623	Approved
0.764	Intermediate Similarity	NPD6079	Approved
0.7614	Intermediate Similarity	NPD5328	Approved
0.7561	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5363	Approved
0.7528	Intermediate Similarity	NPD5785	Approved
0.75	Intermediate Similarity	NPD7331	Phase 2
0.7444	Intermediate Similarity	NPD7515	Phase 2
0.7416	Intermediate Similarity	NPD4753	Phase 2
0.7412	Intermediate Similarity	NPD4223	Phase 3
0.7412	Intermediate Similarity	NPD4221	Approved
0.7407	Intermediate Similarity	NPD8264	Approved
0.7381	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD4202	Approved
0.7312	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD5221	Approved
0.7312	Intermediate Similarity	NPD5222	Approved
0.7292	Intermediate Similarity	NPD5211	Phase 2
0.7273	Intermediate Similarity	NPD5690	Phase 2
0.7241	Intermediate Similarity	NPD3668	Phase 3
0.7241	Intermediate Similarity	NPD4197	Approved
0.7234	Intermediate Similarity	NPD5173	Approved
0.7209	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4269	Approved
0.7209	Intermediate Similarity	NPD4270	Approved
0.7204	Intermediate Similarity	NPD5210	Approved
0.7204	Intermediate Similarity	NPD4629	Approved
0.7159	Intermediate Similarity	NPD5329	Approved
0.7143	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD7341	Phase 2
0.7143	Intermediate Similarity	NPD5141	Approved
0.7128	Intermediate Similarity	NPD4697	Phase 3
0.7126	Intermediate Similarity	NPD5362	Discontinued
0.7125	Intermediate Similarity	NPD4691	Approved
0.7105	Intermediate Similarity	NPD2664	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7748	Approved
0.7083	Intermediate Similarity	NPD5285	Approved
0.7083	Intermediate Similarity	NPD5286	Approved
0.7083	Intermediate Similarity	NPD4696	Approved
0.7079	Intermediate Similarity	NPD5205	Approved
0.7079	Intermediate Similarity	NPD4688	Approved
0.7079	Intermediate Similarity	NPD4138	Approved
0.7079	Intermediate Similarity	NPD7146	Approved
0.7079	Intermediate Similarity	NPD6409	Approved
0.7079	Intermediate Similarity	NPD6684	Approved
0.7079	Intermediate Similarity	NPD5330	Approved
0.7079	Intermediate Similarity	NPD4693	Phase 3
0.7079	Intermediate Similarity	NPD4689	Approved
0.7079	Intermediate Similarity	NPD7521	Approved
0.7079	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD4690	Approved
0.7079	Intermediate Similarity	NPD7334	Approved
0.7079	Intermediate Similarity	NPD4694	Approved
0.7053	Intermediate Similarity	NPD4755	Approved
0.7024	Intermediate Similarity	NPD4756	Discovery
0.701	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD4137	Phase 3
0.6989	Remote Similarity	NPD5778	Approved
0.6989	Remote Similarity	NPD6399	Phase 3
0.6989	Remote Similarity	NPD5779	Approved
0.6979	Remote Similarity	NPD4225	Approved
0.6977	Remote Similarity	NPD4252	Approved
0.6974	Remote Similarity	NPD368	Approved
0.6966	Remote Similarity	NPD1694	Approved
0.6939	Remote Similarity	NPD5226	Approved
0.6939	Remote Similarity	NPD4633	Approved
0.6939	Remote Similarity	NPD5224	Approved
0.6939	Remote Similarity	NPD5225	Approved
0.6932	Remote Similarity	NPD7154	Phase 3
0.6932	Remote Similarity	NPD4788	Approved
0.6923	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD6903	Approved
0.6923	Remote Similarity	NPD4518	Approved
0.6914	Remote Similarity	NPD4747	Approved
0.6907	Remote Similarity	NPD4700	Approved
0.6905	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD5786	Approved
0.6882	Remote Similarity	NPD6411	Approved
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD7902	Approved
0.6875	Remote Similarity	NPD6083	Phase 2
0.6869	Remote Similarity	NPD5175	Approved
0.6869	Remote Similarity	NPD5174	Approved
0.6867	Remote Similarity	NPD4058	Approved
0.686	Remote Similarity	NPD4195	Approved
0.6848	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5695	Phase 3
0.6835	Remote Similarity	NPD3704	Approved
0.6829	Remote Similarity	NPD5276	Approved
0.68	Remote Similarity	NPD287	Approved
0.6786	Remote Similarity	NPD7339	Approved
0.6786	Remote Similarity	NPD6942	Approved
0.6786	Remote Similarity	NPD8039	Approved
0.6782	Remote Similarity	NPD4822	Approved
0.6782	Remote Similarity	NPD4821	Approved
0.6782	Remote Similarity	NPD4819	Approved
0.6782	Remote Similarity	NPD4820	Approved
0.6774	Remote Similarity	NPD4096	Approved
0.6774	Remote Similarity	NPD6698	Approved
0.6774	Remote Similarity	NPD46	Approved
0.6744	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4271	Approved
0.6744	Remote Similarity	NPD4268	Approved
0.6742	Remote Similarity	NPD5332	Approved
0.6742	Remote Similarity	NPD6110	Phase 1
0.6742	Remote Similarity	NPD5331	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD6672	Approved
0.6737	Remote Similarity	NPD5282	Discontinued
0.6735	Remote Similarity	NPD7639	Approved
0.6735	Remote Similarity	NPD7640	Approved
0.6729	Remote Similarity	NPD7115	Discovery
0.6705	Remote Similarity	NPD4790	Discontinued
0.6705	Remote Similarity	NPD5369	Approved
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5281	Approved
0.67	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6924	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6926	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD6929	Approved
0.6633	Remote Similarity	NPD5696	Approved
0.6633	Remote Similarity	NPD7638	Approved
0.663	Remote Similarity	NPD3573	Approved
0.663	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6925	Approved
0.6628	Remote Similarity	NPD5776	Phase 2
0.6625	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD342	Phase 1
0.6602	Remote Similarity	NPD6011	Approved
0.6602	Remote Similarity	NPD5168	Approved
0.6602	Remote Similarity	NPD4730	Approved
0.6602	Remote Similarity	NPD4729	Approved
0.6602	Remote Similarity	NPD6686	Approved
0.6602	Remote Similarity	NPD6899	Approved
0.6602	Remote Similarity	NPD6881	Approved
0.6602	Remote Similarity	NPD5128	Approved
0.6591	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD5368	Approved
0.6591	Remote Similarity	NPD6931	Approved
0.6591	Remote Similarity	NPD6930	Phase 2
0.6591	Remote Similarity	NPD7514	Phase 3
0.6591	Remote Similarity	NPD7332	Phase 2
0.6585	Remote Similarity	NPD6922	Approved
0.6585	Remote Similarity	NPD6923	Approved
0.6569	Remote Similarity	NPD4768	Approved
0.6569	Remote Similarity	NPD5739	Approved
0.6569	Remote Similarity	NPD6402	Approved
0.6569	Remote Similarity	NPD7128	Approved
0.6569	Remote Similarity	NPD4767	Approved
0.6569	Remote Similarity	NPD6675	Approved
0.6566	Remote Similarity	NPD6404	Discontinued
0.6562	Remote Similarity	NPD7900	Approved
0.6562	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD7145	Approved
0.6538	Remote Similarity	NPD6012	Approved
0.6538	Remote Similarity	NPD4194	Approved
0.6538	Remote Similarity	NPD6014	Approved
0.6538	Remote Similarity	NPD4193	Approved
0.6538	Remote Similarity	NPD4191	Approved
0.6538	Remote Similarity	NPD6013	Approved
0.6538	Remote Similarity	NPD4192	Approved
0.6533	Remote Similarity	NPD4219	Approved
0.6526	Remote Similarity	NPD7637	Suspended
0.6517	Remote Similarity	NPD6902	Approved
0.6517	Remote Similarity	NPD4692	Approved
0.6517	Remote Similarity	NPD4139	Approved
0.6512	Remote Similarity	NPD6933	Approved
0.6506	Remote Similarity	NPD7144	Approved
0.6506	Remote Similarity	NPD7143	Approved
0.6505	Remote Similarity	NPD6412	Phase 2
0.6505	Remote Similarity	NPD5701	Approved
0.6477	Remote Similarity	NPD7645	Phase 2
0.6476	Remote Similarity	NPD5250	Approved
0.6476	Remote Similarity	NPD5248	Approved
0.6476	Remote Similarity	NPD5251	Approved
0.6476	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD4634	Approved
0.6476	Remote Similarity	NPD5249	Phase 3
0.6476	Remote Similarity	NPD5169	Approved
0.6476	Remote Similarity	NPD6371	Approved
0.6476	Remote Similarity	NPD7290	Approved
0.6476	Remote Similarity	NPD7102	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