NPASS Compound

Structure

NPC474853 OpenBabel07101718292D 23 25 0 0 1 0 0 0 0 0999 V2000 2.8774 -0.2420 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6822 -3.1632 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1604 0.9871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9350 0.3546 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6167 -0.0652 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1110 0.2268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5170 -0.6990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2319 -1.2827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9758 -1.1407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2946 -2.0472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9288 -0.5587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7225 -2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5276 0.2503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7469 -1.6779 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.1551 -1.0611 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1616 -2.0016 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.3508 -0.4668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8384 -2.0096 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4629 -1.0481 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 2.5464 -2.2787 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4196 -2.8234 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4115 -0.7314 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 11 2 0 0 0 0 2 12 1 0 0 0 0 3 20 1 0 0 0 0 4 20 1 0 0 0 0 5 6 1 0 0 0 0 5 11 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 9 11 1 0 0 0 0 9 14 1 0 0 0 0 10 12 2 0 0 0 0 10 14 1 0 0 0 0 13 6 1 6 0 0 0 13 20 1 0 0 0 0 14 21 1 0 0 0 0 15 17 2 0 0 0 0 15 18 1 0 0 0 0 16 12 1 1 0 0 0 16 18 1 0 0 0 0 16 19 1 0 0 0 0 17 19 1 0 0 0 0 17 20 1 0 0 0 0 18 22 1 1 0 0 0 19 23 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	344.632
LogP:	3.252
LogD:	0.827
LogS:	-2.374
# Rotatable Bonds:	0
TPSA:	54.37
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.55
Synthetic Accessibility Score:	6.111
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.584
MDCK Permeability:	2.572080302343238e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.982
30% Bioavailability (F30%):	0.802

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.456
Plasma Protein Binding (PPB):	63.84111785888672%
Volume Distribution (VD):	1.647
Pgp-substrate:	37.23678207397461%

ADMET: Metabolism

CYP1A2-inhibitor:	0.015
CYP1A2-substrate:	0.509
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.777
CYP2C9-inhibitor:	0.023
CYP2C9-substrate:	0.588
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.704
CYP3A4-inhibitor:	0.094
CYP3A4-substrate:	0.383

ADMET: Excretion

Clearance (CL):	13.718
Half-life (T1/2):	0.102

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.283
Drug-inuced Liver Injury (DILI):	0.905
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.998
Maximum Recommended Daily Dose:	0.639
Skin Sensitization:	0.051
Carcinogencity:	0.479
Eye Corrosion:	0.69
Eye Irritation:	0.124
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC474853

Natural Product ID:	NPC474853
*Common Name:**	Cespitularin F
IUPAC Name:	n.a.
Synonyms:	Cespitularin F
Standard InCHIKey:	PYHGXJSOVZVBAF-MQZXTAGXSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-11-5-6-13-7-8-15-17(20(13,3)4)19(23)16(18(15)22)12(2)10-14(21)9-11/h10,13-14,16,18,21-22H,1,5-9H2,2-4H3/b12-10+/t13-,14?,16+,18+/m1/s1
SMILES:	C=C1CC[C@@H]2CCC3=C(C2(C)C)C(=O)[C@@H](/C(=C/C(C1)O)/C)[C@H]3O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485068
PubChem CID:	11120662
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000129] Alcohols and polyols [CHEMONTID:0001292] Cyclic alcohols and derivatives

*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]
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16495058]
NPO24310	Cespitularia hypotentaculata	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16933873]
NPO2560	Cespitularia taeniata	Species	Xeniidae	Eukaryota	n.a.	Taiwanese soft coral	n.a.	PMID[18052327]
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
IC50	2

Activity Type	# Activity
Cell Line	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1184	Cell Line	Daoy	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[512089]
NPT1183	Cell Line	WiDr	Homo sapiens	IC50	>	20.0	ug.mL-1	PMID[512089]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	16.11	ug ml-1	PMID[512090]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	50.0	ug ml-1	PMID[512090]
NPT168	Cell Line	P388	Mus musculus	ED50	>	50.0	ug ml-1	PMID[512090]

☑ 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 NPC474853 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	1124
0.2-0.3	5210
0.3-0.4	13316
0.4-0.5	11167
0.5-0.6	6537
0.6-0.7	4200
0.7-0.8	885
0.8-0.85	69
0.85-0.9	11
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC179006
0.9398	High Similarity	NPC474854
0.9157	High Similarity	NPC194417
0.908	High Similarity	NPC53685
0.8875	High Similarity	NPC475994
0.8706	High Similarity	NPC476043
0.8659	High Similarity	NPC45495
0.8621	High Similarity	NPC472971
0.8621	High Similarity	NPC472970
0.8537	High Similarity	NPC308038
0.8537	High Similarity	NPC7232
0.8523	High Similarity	NPC48010
0.8488	Intermediate Similarity	NPC470955
0.8434	Intermediate Similarity	NPC104120
0.8434	Intermediate Similarity	NPC157895
0.8434	Intermediate Similarity	NPC148685
0.8409	Intermediate Similarity	NPC309603
0.8409	Intermediate Similarity	NPC473999
0.8395	Intermediate Similarity	NPC263582
0.8391	Intermediate Similarity	NPC312561
0.8372	Intermediate Similarity	NPC471224
0.8372	Intermediate Similarity	NPC474083
0.8352	Intermediate Similarity	NPC472932
0.8333	Intermediate Similarity	NPC474736
0.8333	Intermediate Similarity	NPC136150
0.8315	Intermediate Similarity	NPC69622
0.8313	Intermediate Similarity	NPC281138
0.8295	Intermediate Similarity	NPC328313
0.8293	Intermediate Similarity	NPC74995
0.8276	Intermediate Similarity	NPC31564
0.8276	Intermediate Similarity	NPC474733
0.8276	Intermediate Similarity	NPC145879
0.8276	Intermediate Similarity	NPC474732
0.8276	Intermediate Similarity	NPC474778
0.8276	Intermediate Similarity	NPC469994
0.8276	Intermediate Similarity	NPC472974
0.8272	Intermediate Similarity	NPC114236
0.8261	Intermediate Similarity	NPC117133
0.8256	Intermediate Similarity	NPC329043
0.8256	Intermediate Similarity	NPC214043
0.8256	Intermediate Similarity	NPC85774
0.8256	Intermediate Similarity	NPC473246
0.8256	Intermediate Similarity	NPC58841
0.8256	Intermediate Similarity	NPC161423
0.8256	Intermediate Similarity	NPC227064
0.8256	Intermediate Similarity	NPC321187
0.825	Intermediate Similarity	NPC186042
0.8235	Intermediate Similarity	NPC93590
0.8222	Intermediate Similarity	NPC473998
0.8222	Intermediate Similarity	NPC475806
0.8214	Intermediate Similarity	NPC138492
0.8214	Intermediate Similarity	NPC233352
0.8214	Intermediate Similarity	NPC172013
0.8214	Intermediate Similarity	NPC824
0.8214	Intermediate Similarity	NPC2482
0.8202	Intermediate Similarity	NPC123912
0.8202	Intermediate Similarity	NPC472477
0.8202	Intermediate Similarity	NPC472475
0.8202	Intermediate Similarity	NPC2983
0.8202	Intermediate Similarity	NPC170775
0.8202	Intermediate Similarity	NPC214387
0.8202	Intermediate Similarity	NPC119416
0.8193	Intermediate Similarity	NPC478122
0.8193	Intermediate Similarity	NPC178852
0.8193	Intermediate Similarity	NPC62336
0.8193	Intermediate Similarity	NPC297996
0.8182	Intermediate Similarity	NPC475740
0.8182	Intermediate Similarity	NPC272039
0.8182	Intermediate Similarity	NPC58063
0.8182	Intermediate Similarity	NPC220930
0.8171	Intermediate Similarity	NPC470525
0.8161	Intermediate Similarity	NPC476426
0.8161	Intermediate Similarity	NPC469948
0.8161	Intermediate Similarity	NPC15807
0.8161	Intermediate Similarity	NPC36350
0.8148	Intermediate Similarity	NPC215050
0.814	Intermediate Similarity	NPC474748
0.8132	Intermediate Similarity	NPC472930
0.8132	Intermediate Similarity	NPC472942
0.8132	Intermediate Similarity	NPC69454
0.8132	Intermediate Similarity	NPC109305
0.8132	Intermediate Similarity	NPC115021
0.8118	Intermediate Similarity	NPC14151
0.8118	Intermediate Similarity	NPC121984
0.8118	Intermediate Similarity	NPC116797
0.8111	Intermediate Similarity	NPC477147
0.8111	Intermediate Similarity	NPC232426
0.8111	Intermediate Similarity	NPC281942
0.8111	Intermediate Similarity	NPC477149
0.8095	Intermediate Similarity	NPC19900
0.8095	Intermediate Similarity	NPC152061
0.809	Intermediate Similarity	NPC471722
0.8085	Intermediate Similarity	NPC471717
0.8085	Intermediate Similarity	NPC197386
0.8085	Intermediate Similarity	NPC235464
0.8085	Intermediate Similarity	NPC166745
0.8072	Intermediate Similarity	NPC86917
0.8072	Intermediate Similarity	NPC197659
0.8068	Intermediate Similarity	NPC475022
0.8068	Intermediate Similarity	NPC222613
0.8068	Intermediate Similarity	NPC472985
0.8068	Intermediate Similarity	NPC118648
0.8068	Intermediate Similarity	NPC472986
0.8049	Intermediate Similarity	NPC474011
0.8046	Intermediate Similarity	NPC237712
0.8046	Intermediate Similarity	NPC7927
0.8046	Intermediate Similarity	NPC476412
0.8046	Intermediate Similarity	NPC230527
0.8046	Intermediate Similarity	NPC165064
0.8046	Intermediate Similarity	NPC59453
0.8046	Intermediate Similarity	NPC221758
0.8046	Intermediate Similarity	NPC82902
0.8043	Intermediate Similarity	NPC8993
0.8023	Intermediate Similarity	NPC20262
0.8023	Intermediate Similarity	NPC158411
0.8023	Intermediate Similarity	NPC256750
0.8023	Intermediate Similarity	NPC151519
0.8023	Intermediate Similarity	NPC46881
0.8023	Intermediate Similarity	NPC38796
0.8022	Intermediate Similarity	NPC141831
0.8022	Intermediate Similarity	NPC63748
0.8022	Intermediate Similarity	NPC131872
0.8022	Intermediate Similarity	NPC233116
0.8	Intermediate Similarity	NPC271104
0.8	Intermediate Similarity	NPC31985
0.8	Intermediate Similarity	NPC477943
0.8	Intermediate Similarity	NPC472983
0.8	Intermediate Similarity	NPC472478
0.8	Intermediate Similarity	NPC26959
0.8	Intermediate Similarity	NPC186688
0.8	Intermediate Similarity	NPC306095
0.8	Intermediate Similarity	NPC1015
0.8	Intermediate Similarity	NPC472489
0.8	Intermediate Similarity	NPC268406
0.7979	Intermediate Similarity	NPC53844
0.7978	Intermediate Similarity	NPC317590
0.7978	Intermediate Similarity	NPC472484
0.7978	Intermediate Similarity	NPC287079
0.7978	Intermediate Similarity	NPC136548
0.7978	Intermediate Similarity	NPC472481
0.7978	Intermediate Similarity	NPC472482
0.7976	Intermediate Similarity	NPC471409
0.7976	Intermediate Similarity	NPC275494
0.7957	Intermediate Similarity	NPC174948
0.7957	Intermediate Similarity	NPC259286
0.7957	Intermediate Similarity	NPC271195
0.7957	Intermediate Similarity	NPC318282
0.7957	Intermediate Similarity	NPC173875
0.7957	Intermediate Similarity	NPC469995
0.7955	Intermediate Similarity	NPC274724
0.7955	Intermediate Similarity	NPC474218
0.7955	Intermediate Similarity	NPC79573
0.7952	Intermediate Similarity	NPC469646
0.7935	Intermediate Similarity	NPC477520
0.7935	Intermediate Similarity	NPC250575
0.7935	Intermediate Similarity	NPC134826
0.7931	Intermediate Similarity	NPC476082
0.7931	Intermediate Similarity	NPC193198
0.7931	Intermediate Similarity	NPC470165
0.7931	Intermediate Similarity	NPC278648
0.7931	Intermediate Similarity	NPC105173
0.7931	Intermediate Similarity	NPC62214
0.7917	Intermediate Similarity	NPC472924
0.7912	Intermediate Similarity	NPC320026
0.7912	Intermediate Similarity	NPC230332
0.7912	Intermediate Similarity	NPC472476
0.7912	Intermediate Similarity	NPC85173
0.7907	Intermediate Similarity	NPC6663
0.7907	Intermediate Similarity	NPC470298
0.7889	Intermediate Similarity	NPC474677
0.7889	Intermediate Similarity	NPC328539
0.7889	Intermediate Similarity	NPC471724
0.7889	Intermediate Similarity	NPC249889
0.7889	Intermediate Similarity	NPC471791
0.7889	Intermediate Similarity	NPC53911
0.7889	Intermediate Similarity	NPC53454
0.7889	Intermediate Similarity	NPC193843
0.7889	Intermediate Similarity	NPC471793
0.7889	Intermediate Similarity	NPC476796
0.7882	Intermediate Similarity	NPC472490
0.7872	Intermediate Similarity	NPC29152
0.7872	Intermediate Similarity	NPC472941
0.7872	Intermediate Similarity	NPC456
0.7872	Intermediate Similarity	NPC184065
0.7872	Intermediate Similarity	NPC249954
0.7872	Intermediate Similarity	NPC328371
0.7865	Intermediate Similarity	NPC327115
0.7865	Intermediate Similarity	NPC198761
0.7865	Intermediate Similarity	NPC94666
0.7865	Intermediate Similarity	NPC472479
0.7865	Intermediate Similarity	NPC72133
0.7865	Intermediate Similarity	NPC473226
0.7865	Intermediate Similarity	NPC82979
0.7865	Intermediate Similarity	NPC51014
0.7857	Intermediate Similarity	NPC471061
0.7857	Intermediate Similarity	NPC276769
0.7857	Intermediate Similarity	NPC257666
0.7857	Intermediate Similarity	NPC266193
0.7849	Intermediate Similarity	NPC473162
0.7849	Intermediate Similarity	NPC474690

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 NPC474853 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	160
0.1-0.2	1738
0.2-0.3	3870
0.3-0.4	2317
0.4-0.5	640
0.5-0.6	262
0.6-0.7	135
0.7-0.8	28
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
0.8256	Intermediate Similarity	NPD3666	Approved
0.8256	Intermediate Similarity	NPD3133	Approved
0.8256	Intermediate Similarity	NPD3665	Phase 1
0.8046	Intermediate Similarity	NPD4786	Approved
0.8023	Intermediate Similarity	NPD3667	Approved
0.7865	Intermediate Similarity	NPD3618	Phase 1
0.7865	Intermediate Similarity	NPD4623	Approved
0.7865	Intermediate Similarity	NPD5279	Phase 3
0.7865	Intermediate Similarity	NPD4519	Discontinued
0.7816	Intermediate Similarity	NPD4223	Phase 3
0.7816	Intermediate Similarity	NPD4221	Approved
0.7802	Intermediate Similarity	NPD5328	Approved
0.7802	Intermediate Similarity	NPD4753	Phase 2
0.7742	Intermediate Similarity	NPD4202	Approved
0.764	Intermediate Similarity	NPD4197	Approved
0.7634	Intermediate Similarity	NPD6079	Approved
0.7556	Intermediate Similarity	NPD1696	Phase 3
0.7556	Intermediate Similarity	NPD5329	Approved
0.7556	Intermediate Similarity	NPD5363	Approved
0.7527	Intermediate Similarity	NPD5785	Approved
0.7475	Intermediate Similarity	NPD5211	Phase 2
0.7473	Intermediate Similarity	NPD4688	Approved
0.7473	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5280	Approved
0.7473	Intermediate Similarity	NPD4693	Phase 3
0.7473	Intermediate Similarity	NPD5205	Approved
0.7473	Intermediate Similarity	NPD4690	Approved
0.7473	Intermediate Similarity	NPD4694	Approved
0.7473	Intermediate Similarity	NPD4138	Approved
0.7473	Intermediate Similarity	NPD5690	Phase 2
0.7473	Intermediate Similarity	NPD4689	Approved
0.7423	Intermediate Similarity	NPD4755	Approved
0.7416	Intermediate Similarity	NPD4270	Approved
0.7416	Intermediate Similarity	NPD4269	Approved
0.7396	Intermediate Similarity	NPD5210	Approved
0.7396	Intermediate Similarity	NPD4629	Approved
0.7386	Intermediate Similarity	NPD4695	Discontinued
0.7356	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD5362	Discontinued
0.7327	Intermediate Similarity	NPD5141	Approved
0.732	Intermediate Similarity	NPD5221	Approved
0.732	Intermediate Similarity	NPD5222	Approved
0.732	Intermediate Similarity	NPD4697	Phase 3
0.732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD7146	Approved
0.7283	Intermediate Similarity	NPD7521	Approved
0.7283	Intermediate Similarity	NPD6409	Approved
0.7283	Intermediate Similarity	NPD5330	Approved
0.7283	Intermediate Similarity	NPD7334	Approved
0.7283	Intermediate Similarity	NPD6684	Approved
0.7273	Intermediate Similarity	NPD5286	Approved
0.7273	Intermediate Similarity	NPD4700	Approved
0.7273	Intermediate Similarity	NPD4696	Approved
0.7273	Intermediate Similarity	NPD5285	Approved
0.7263	Intermediate Similarity	NPD7515	Phase 2
0.7253	Intermediate Similarity	NPD3668	Phase 3
0.7245	Intermediate Similarity	NPD5173	Approved
0.7245	Intermediate Similarity	NPD6084	Phase 2
0.7245	Intermediate Similarity	NPD6083	Phase 2
0.7216	Intermediate Similarity	NPD5695	Phase 3
0.72	Intermediate Similarity	NPD5223	Approved
0.7191	Intermediate Similarity	NPD4252	Approved
0.7188	Intermediate Similarity	NPD6399	Phase 3
0.7159	Intermediate Similarity	NPD3617	Approved
0.7143	Intermediate Similarity	NPD4788	Approved
0.7129	Intermediate Similarity	NPD5226	Approved
0.7129	Intermediate Similarity	NPD5225	Approved
0.7129	Intermediate Similarity	NPD4633	Approved
0.7129	Intermediate Similarity	NPD5224	Approved
0.7128	Intermediate Similarity	NPD4518	Approved
0.7128	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD6903	Approved
0.7126	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5282	Discontinued
0.7097	Intermediate Similarity	NPD5786	Approved
0.7083	Intermediate Similarity	NPD5284	Approved
0.7083	Intermediate Similarity	NPD5281	Approved
0.7079	Intermediate Similarity	NPD4195	Approved
0.7064	Intermediate Similarity	NPD7115	Discovery
0.7059	Intermediate Similarity	NPD4754	Approved
0.7059	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7021	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD7339	Approved
0.7011	Intermediate Similarity	NPD6942	Approved
0.701	Intermediate Similarity	NPD5778	Approved
0.701	Intermediate Similarity	NPD5779	Approved
0.7	Intermediate Similarity	NPD5696	Approved
0.7	Intermediate Similarity	NPD4225	Approved
0.6981	Remote Similarity	NPD6371	Approved
0.6981	Remote Similarity	NPD4634	Approved
0.6979	Remote Similarity	NPD4096	Approved
0.6947	Remote Similarity	NPD5737	Approved
0.6947	Remote Similarity	NPD6672	Approved
0.6941	Remote Similarity	NPD4747	Approved
0.6939	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD4139	Approved
0.6923	Remote Similarity	NPD6402	Approved
0.6923	Remote Similarity	NPD4768	Approved
0.6923	Remote Similarity	NPD7128	Approved
0.6923	Remote Similarity	NPD5369	Approved
0.6923	Remote Similarity	NPD4692	Approved
0.6923	Remote Similarity	NPD4767	Approved
0.6923	Remote Similarity	NPD5739	Approved
0.6923	Remote Similarity	NPD6675	Approved
0.6907	Remote Similarity	NPD6411	Approved
0.6867	Remote Similarity	NPD7331	Phase 2
0.6857	Remote Similarity	NPD5701	Approved
0.6857	Remote Similarity	NPD5697	Approved
0.6848	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD5133	Approved
0.6824	Remote Similarity	NPD4137	Phase 3
0.6818	Remote Similarity	NPD8264	Approved
0.6813	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD1694	Approved
0.6792	Remote Similarity	NPD6881	Approved
0.6792	Remote Similarity	NPD6899	Approved
0.6792	Remote Similarity	NPD6011	Approved
0.6792	Remote Similarity	NPD4730	Approved
0.6792	Remote Similarity	NPD4729	Approved
0.6792	Remote Similarity	NPD7320	Approved
0.6792	Remote Similarity	NPD5128	Approved
0.6778	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD7154	Phase 3
0.6774	Remote Similarity	NPD5332	Approved
0.6774	Remote Similarity	NPD5331	Approved
0.6771	Remote Similarity	NPD5208	Approved
0.6765	Remote Similarity	NPD7640	Approved
0.6765	Remote Similarity	NPD7639	Approved
0.6747	Remote Similarity	NPD7341	Phase 2
0.6744	Remote Similarity	NPD4691	Approved
0.6739	Remote Similarity	NPD4790	Discontinued
0.6735	Remote Similarity	NPD7637	Suspended
0.6735	Remote Similarity	NPD5693	Phase 1
0.6733	Remote Similarity	NPD7902	Approved
0.6729	Remote Similarity	NPD6373	Approved
0.6729	Remote Similarity	NPD6014	Approved
0.6729	Remote Similarity	NPD6372	Approved
0.6729	Remote Similarity	NPD6013	Approved
0.6729	Remote Similarity	NPD6012	Approved
0.6705	Remote Similarity	NPD6926	Approved
0.6705	Remote Similarity	NPD6924	Approved
0.6705	Remote Similarity	NPD4687	Approved
0.6705	Remote Similarity	NPD5733	Approved
0.6703	Remote Similarity	NPD6929	Approved
0.6701	Remote Similarity	NPD6080	Approved
0.6701	Remote Similarity	NPD6904	Approved
0.6701	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6101	Approved
0.6701	Remote Similarity	NPD6673	Approved
0.6701	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD6412	Phase 2
0.6667	Remote Similarity	NPD7290	Approved
0.6667	Remote Similarity	NPD7638	Approved
0.6667	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD7102	Approved
0.6667	Remote Similarity	NPD5248	Approved
0.6667	Remote Similarity	NPD6883	Approved
0.6667	Remote Similarity	NPD5209	Approved
0.6667	Remote Similarity	NPD5247	Approved
0.6667	Remote Similarity	NPD5135	Approved
0.6667	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5276	Approved
0.6667	Remote Similarity	NPD5251	Approved
0.6667	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5250	Approved
0.6667	Remote Similarity	NPD5249	Phase 3
0.6636	Remote Similarity	NPD5168	Approved
0.6633	Remote Similarity	NPD5207	Approved
0.6633	Remote Similarity	NPD5692	Phase 3
0.6632	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.663	Remote Similarity	NPD4819	Approved
0.663	Remote Similarity	NPD4822	Approved
0.663	Remote Similarity	NPD7332	Phase 2
0.663	Remote Similarity	NPD4821	Approved
0.663	Remote Similarity	NPD4820	Approved
0.663	Remote Similarity	NPD6930	Phase 2
0.663	Remote Similarity	NPD6931	Approved
0.6606	Remote Similarity	NPD6847	Approved
0.6606	Remote Similarity	NPD8130	Phase 1
0.6606	Remote Similarity	NPD6650	Approved
0.6606	Remote Similarity	NPD6617	Approved
0.6606	Remote Similarity	NPD5215	Approved
0.6606	Remote Similarity	NPD5127	Approved
0.6606	Remote Similarity	NPD5217	Approved
0.6606	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5216	Approved
0.6606	Remote Similarity	NPD6869	Approved
0.6606	Remote Similarity	NPD6649	Approved
0.6602	Remote Similarity	NPD6404	Discontinued
0.6593	Remote Similarity	NPD4271	Approved
0.6593	Remote Similarity	NPD4268	Approved
0.6585	Remote Similarity	NPD368	Approved
0.6566	Remote Similarity	NPD5694	Approved
0.6566	Remote Similarity	NPD6050	Approved
0.6562	Remote Similarity	NPD6098	Approved
0.6556	Remote Similarity	NPD6933	Approved
0.6548	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD6882	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