NPASS Compound

Structure

NPC476082 OpenBabel07101718202D 31 33 0 0 1 0 0 0 0 0999 V2000 -8.7466 1.2273 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5656 -0.4953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7576 1.4364 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7631 1.5409 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 -4.1808 -0.6499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5765 -0.2862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5820 -0.1817 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 -3.6808 1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7026 1.4945 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2026 -0.8578 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8717 -1.6009 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 -8.1588 0.4183 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1643 0.5228 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -5.1753 0.7319 0.0000 C 0 0 2 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 1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1808 0.8364 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 1 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 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.5116 0.0933 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.8499 -1.3930 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 18 1 0 0 0 0 2 18 1 0 0 0 0 3 19 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 9 10 1 0 0 0 0 9 21 2 0 0 0 0 11 12 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 22 1 0 0 0 0 14 27 1 0 0 0 0 15 16 1 0 0 0 0 15 28 1 0 0 0 0 16 29 1 0 0 0 0 17 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 20 4 1 1 0 0 0 20 24 1 0 0 0 0 21 27 1 0 0 0 0 22 30 1 6 0 0 0 23 10 1 1 0 0 0 23 25 1 0 0 0 0 23 26 1 0 0 0 0 24 28 1 1 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 31 2 0 0 0 0 27 5 1 6 0 0 0 28 6 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.36
Volume:	488.272
LogP:	5.876
LogD:	5.655
LogS:	-5.555
# Rotatable Bonds:	8
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.451
Synthetic Accessibility Score:	4.791
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.615
MDCK Permeability:	1.3713065527554136e-05
Pgp-inhibitor:	0.112
Pgp-substrate:	0.232
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.967
30% Bioavailability (F30%):	0.15

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.351
Plasma Protein Binding (PPB):	96.45782470703125%
Volume Distribution (VD):	1.235
Pgp-substrate:	1.3961000442504883%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.392
CYP2C19-inhibitor:	0.054
CYP2C19-substrate:	0.908
CYP2C9-inhibitor:	0.252
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.029
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.901

ADMET: Excretion

Clearance (CL):	12.139
Half-life (T1/2):	0.106

ADMET: Toxicity

hERG Blockers:	0.008
Human Hepatotoxicity (H-HT):	0.251
Drug-inuced Liver Injury (DILI):	0.12
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.706
Maximum Recommended Daily Dose:	0.372
Skin Sensitization:	0.063
Carcinogencity:	0.3
Eye Corrosion:	0.311
Eye Irritation:	0.136
Respiratory Toxicity:	0.978

Download Data

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

Natural Product: NPC476082

Natural Product ID:	NPC476082
*Common Name:**	(2S,6S,8As)-2-[(1S,2R,3R)-3-[(2R)-5,6-Dimethylheptan-2-Yl]-2-(2-Hydroxyethyl)-2-Methylcyclopentyl]-6-Hydroxy-8A-Methyl-2,3,5,6,7,8-Hexahydronaphthalen-1-One
IUPAC Name:	(2S,6S,8aS)-2-[(1S,2R,3R)-3-[(2R)-5,6-dimethylheptan-2-yl]-2-(2-hydroxyethyl)-2-methylcyclopentyl]-6-hydroxy-8a-methyl-2,3,5,6,7,8-hexahydronaphthalen-1-one
Synonyms:
Standard InCHIKey:	IWHGIUPHPWHJHD-SFEXJKSVSA-N
Standard InCHI:	InChI=1S/C28H48O3/c1-18(2)19(3)7-8-20(4)24-11-12-25(28(24,6)15-16-29)23-10-9-21-17-22(30)13-14-27(21,5)26(23)31/h9,18-20,22-25,29-30H,7-8,10-17H2,1-6H3/t19?,20-,22+,23+,24-,25+,27+,28-/m1/s1
SMILES:	OCC[C@]1(C)[C@H](CC[C@H]1[C@@H]1CC=C2[C@](C1=O)(C)CC[C@@H](C2)O)[C@@H](CCC(C(C)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL525172
PubChem CID:	44583849
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids

*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
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[16724859]
NPO15548	Sinularia leptoclados	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7825	Sinularia lochmodes	Species	Alcyoniidae	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
IC50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT65	Cell Line	HepG2	Homo sapiens	IC50	=	14.1	ug.mL-1	PMID[510363]
NPT81	Cell Line	A549	Homo sapiens	IC50	=	16.8	ug.mL-1	PMID[510363]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	15.0	ug.mL-1	PMID[510363]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	15.7	ug.mL-1	PMID[510363]

☑ 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 NPC476082 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	141
0.1-0.2	1027
0.2-0.3	5130
0.3-0.4	15046
0.4-0.5	8296
0.5-0.6	6716
0.6-0.7	4780
0.7-0.8	1378
0.8-0.85	142
0.85-0.9	35
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC278648
0.9747	High Similarity	NPC202868
0.9375	High Similarity	NPC59453
0.9375	High Similarity	NPC221758
0.9157	High Similarity	NPC53911
0.9146	High Similarity	NPC51014
0.9146	High Similarity	NPC145879
0.9146	High Similarity	NPC474778
0.9146	High Similarity	NPC474732
0.9146	High Similarity	NPC474733
0.9146	High Similarity	NPC31564
0.9125	High Similarity	NPC151519
0.9048	High Similarity	NPC86319
0.9048	High Similarity	NPC186688
0.9048	High Similarity	NPC275740
0.9036	High Similarity	NPC475740
0.9036	High Similarity	NPC58063
0.9024	High Similarity	NPC469948
0.8929	High Similarity	NPC328539
0.8929	High Similarity	NPC471722
0.8929	High Similarity	NPC143767
0.8929	High Similarity	NPC131470
0.8929	High Similarity	NPC328313
0.8916	High Similarity	NPC155011
0.8916	High Similarity	NPC222613
0.8916	High Similarity	NPC20688
0.8916	High Similarity	NPC475022
0.8916	High Similarity	NPC118648
0.8902	High Similarity	NPC214043
0.8902	High Similarity	NPC473246
0.8902	High Similarity	NPC85774
0.8902	High Similarity	NPC82902
0.8875	High Similarity	NPC164999
0.8824	High Similarity	NPC31985
0.8824	High Similarity	NPC32830
0.8824	High Similarity	NPC474245
0.8824	High Similarity	NPC1015
0.8824	High Similarity	NPC268406
0.8824	High Similarity	NPC76879
0.8824	High Similarity	NPC26959
0.8795	High Similarity	NPC471224
0.8795	High Similarity	NPC474218
0.8795	High Similarity	NPC474083
0.8736	High Similarity	NPC69454
0.8721	High Similarity	NPC183283
0.8721	High Similarity	NPC48010
0.869	High Similarity	NPC94755
0.869	High Similarity	NPC469994
0.869	High Similarity	NPC72133
0.8675	High Similarity	NPC165064
0.8675	High Similarity	NPC472265
0.8636	High Similarity	NPC166906
0.8621	High Similarity	NPC168027
0.8621	High Similarity	NPC63748
0.8621	High Similarity	NPC185936
0.8605	High Similarity	NPC473999
0.8605	High Similarity	NPC309603
0.8605	High Similarity	NPC477943
0.8588	High Similarity	NPC474684
0.8588	High Similarity	NPC159046
0.8588	High Similarity	NPC233836
0.8588	High Similarity	NPC187376
0.8588	High Similarity	NPC142361
0.8588	High Similarity	NPC90652
0.8588	High Similarity	NPC317590
0.8571	High Similarity	NPC470574
0.8556	High Similarity	NPC190554
0.8539	High Similarity	NPC259286
0.8539	High Similarity	NPC472932
0.8539	High Similarity	NPC127063
0.8539	High Similarity	NPC470016
0.8539	High Similarity	NPC317586
0.8539	High Similarity	NPC469599
0.8537	High Similarity	NPC136150
0.8523	High Similarity	NPC206810
0.8523	High Similarity	NPC477520
0.8523	High Similarity	NPC472930
0.8519	High Similarity	NPC477371
0.8506	High Similarity	NPC69622
0.8506	High Similarity	NPC191684
0.8488	Intermediate Similarity	NPC471724
0.8488	Intermediate Similarity	NPC193360
0.8488	Intermediate Similarity	NPC470417
0.8488	Intermediate Similarity	NPC242864
0.8471	Intermediate Similarity	NPC473168
0.8471	Intermediate Similarity	NPC327115
0.8471	Intermediate Similarity	NPC89077
0.8471	Intermediate Similarity	NPC55309
0.8471	Intermediate Similarity	NPC28252
0.8452	Intermediate Similarity	NPC33913
0.8452	Intermediate Similarity	NPC237712
0.8452	Intermediate Similarity	NPC329043
0.8452	Intermediate Similarity	NPC161423
0.8452	Intermediate Similarity	NPC227064
0.8452	Intermediate Similarity	NPC180834
0.8452	Intermediate Similarity	NPC321187
0.8452	Intermediate Similarity	NPC58841
0.8444	Intermediate Similarity	NPC96859
0.8444	Intermediate Similarity	NPC249954
0.8444	Intermediate Similarity	NPC328162
0.8444	Intermediate Similarity	NPC173272
0.8444	Intermediate Similarity	NPC305483
0.8434	Intermediate Similarity	NPC260956
0.8427	Intermediate Similarity	NPC196485
0.8427	Intermediate Similarity	NPC245972
0.8415	Intermediate Similarity	NPC472478
0.8415	Intermediate Similarity	NPC2482
0.8409	Intermediate Similarity	NPC475806
0.8409	Intermediate Similarity	NPC272746
0.8409	Intermediate Similarity	NPC473998
0.8395	Intermediate Similarity	NPC82635
0.8391	Intermediate Similarity	NPC475921
0.8391	Intermediate Similarity	NPC472971
0.8391	Intermediate Similarity	NPC84271
0.8391	Intermediate Similarity	NPC102414
0.8391	Intermediate Similarity	NPC474704
0.8391	Intermediate Similarity	NPC123912
0.8391	Intermediate Similarity	NPC119416
0.8391	Intermediate Similarity	NPC128496
0.8391	Intermediate Similarity	NPC77168
0.8391	Intermediate Similarity	NPC472970
0.8391	Intermediate Similarity	NPC2983
0.8375	Intermediate Similarity	NPC321016
0.8375	Intermediate Similarity	NPC107059
0.8375	Intermediate Similarity	NPC321381
0.8372	Intermediate Similarity	NPC472481
0.8372	Intermediate Similarity	NPC93778
0.8372	Intermediate Similarity	NPC141292
0.8372	Intermediate Similarity	NPC472484
0.8372	Intermediate Similarity	NPC472482
0.8372	Intermediate Similarity	NPC96496
0.8372	Intermediate Similarity	NPC136548
0.837	Intermediate Similarity	NPC112167
0.837	Intermediate Similarity	NPC83709
0.837	Intermediate Similarity	NPC15390
0.837	Intermediate Similarity	NPC110149
0.8353	Intermediate Similarity	NPC36350
0.8352	Intermediate Similarity	NPC43747
0.8333	Intermediate Similarity	NPC174948
0.8333	Intermediate Similarity	NPC173875
0.8333	Intermediate Similarity	NPC318282
0.8333	Intermediate Similarity	NPC473170
0.8333	Intermediate Similarity	NPC48330
0.8333	Intermediate Similarity	NPC469995
0.8333	Intermediate Similarity	NPC105173
0.8333	Intermediate Similarity	NPC64600
0.8315	Intermediate Similarity	NPC474736
0.8315	Intermediate Similarity	NPC472942
0.8315	Intermediate Similarity	NPC12722
0.8315	Intermediate Similarity	NPC475255
0.8315	Intermediate Similarity	NPC250575
0.8315	Intermediate Similarity	NPC477855
0.8313	Intermediate Similarity	NPC38350
0.8313	Intermediate Similarity	NPC147066
0.8313	Intermediate Similarity	NPC473420
0.8313	Intermediate Similarity	NPC14151
0.8313	Intermediate Similarity	NPC477372
0.8313	Intermediate Similarity	NPC201912
0.8295	Intermediate Similarity	NPC171441
0.8295	Intermediate Similarity	NPC320026
0.8295	Intermediate Similarity	NPC85173
0.8295	Intermediate Similarity	NPC126993
0.8293	Intermediate Similarity	NPC472490
0.8293	Intermediate Similarity	NPC215843
0.8276	Intermediate Similarity	NPC310752
0.8276	Intermediate Similarity	NPC44181
0.8276	Intermediate Similarity	NPC292491
0.8272	Intermediate Similarity	NPC197659
0.8272	Intermediate Similarity	NPC318495
0.8272	Intermediate Similarity	NPC276769
0.8272	Intermediate Similarity	NPC155986
0.8272	Intermediate Similarity	NPC198968
0.8272	Intermediate Similarity	NPC325946
0.8261	Intermediate Similarity	NPC114274
0.8261	Intermediate Similarity	NPC197386
0.825	Intermediate Similarity	NPC22105
0.825	Intermediate Similarity	NPC285893
0.825	Intermediate Similarity	NPC136188
0.825	Intermediate Similarity	NPC28657
0.825	Intermediate Similarity	NPC162742
0.825	Intermediate Similarity	NPC304309
0.825	Intermediate Similarity	NPC288035
0.825	Intermediate Similarity	NPC230301
0.825	Intermediate Similarity	NPC134847
0.8242	Intermediate Similarity	NPC328371
0.8242	Intermediate Similarity	NPC192428
0.8242	Intermediate Similarity	NPC471463
0.8242	Intermediate Similarity	NPC49371
0.8235	Intermediate Similarity	NPC25833
0.8228	Intermediate Similarity	NPC474140
0.8222	Intermediate Similarity	NPC8993
0.8222	Intermediate Similarity	NPC292793
0.8222	Intermediate Similarity	NPC111015
0.8214	Intermediate Similarity	NPC212083
0.8214	Intermediate Similarity	NPC310989
0.8214	Intermediate Similarity	NPC133391
0.8214	Intermediate Similarity	NPC328351
0.8214	Intermediate Similarity	NPC48362
0.8202	Intermediate Similarity	NPC86266
0.8202	Intermediate Similarity	NPC233116

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 NPC476082 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	136
0.1-0.2	1420
0.2-0.3	4099
0.3-0.4	2437
0.4-0.5	573
0.5-0.6	185
0.6-0.7	160
0.7-0.8	131
0.8-0.85	6
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9375	High Similarity	NPD4786	Approved
0.9125	High Similarity	NPD3667	Approved
0.9048	High Similarity	NPD5328	Approved
0.8837	High Similarity	NPD6079	Approved
0.8471	Intermediate Similarity	NPD3618	Phase 1
0.8452	Intermediate Similarity	NPD3666	Approved
0.8452	Intermediate Similarity	NPD3133	Approved
0.8452	Intermediate Similarity	NPD3665	Phase 1
0.8315	Intermediate Similarity	NPD6399	Phase 3
0.8256	Intermediate Similarity	NPD5279	Phase 3
0.825	Intermediate Similarity	NPD6942	Approved
0.825	Intermediate Similarity	NPD7339	Approved
0.8242	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD4697	Phase 3
0.8242	Intermediate Similarity	NPD5221	Approved
0.8242	Intermediate Similarity	NPD5222	Approved
0.8235	Intermediate Similarity	NPD3668	Phase 3
0.8152	Intermediate Similarity	NPD5173	Approved
0.8152	Intermediate Similarity	NPD4755	Approved
0.8111	Intermediate Similarity	NPD4202	Approved
0.8	Intermediate Similarity	NPD4221	Approved
0.8	Intermediate Similarity	NPD4223	Phase 3
0.7979	Intermediate Similarity	NPD5286	Approved
0.7979	Intermediate Similarity	NPD5285	Approved
0.7979	Intermediate Similarity	NPD4700	Approved
0.7979	Intermediate Similarity	NPD4696	Approved
0.7978	Intermediate Similarity	NPD4753	Phase 2
0.7931	Intermediate Similarity	NPD5329	Approved
0.7927	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6926	Approved
0.7901	Intermediate Similarity	NPD6924	Approved
0.7895	Intermediate Similarity	NPD5223	Approved
0.7816	Intermediate Similarity	NPD4197	Approved
0.7812	Intermediate Similarity	NPD5211	Phase 2
0.7812	Intermediate Similarity	NPD5224	Approved
0.7812	Intermediate Similarity	NPD5226	Approved
0.7812	Intermediate Similarity	NPD5225	Approved
0.7812	Intermediate Similarity	NPD4633	Approved
0.7755	Intermediate Similarity	NPD5739	Approved
0.7755	Intermediate Similarity	NPD7128	Approved
0.7755	Intermediate Similarity	NPD6675	Approved
0.7755	Intermediate Similarity	NPD6402	Approved
0.7732	Intermediate Similarity	NPD5174	Approved
0.7732	Intermediate Similarity	NPD5175	Approved
0.7732	Intermediate Similarity	NPD4754	Approved
0.7727	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6933	Approved
0.7701	Intermediate Similarity	NPD4788	Approved
0.7654	Intermediate Similarity	NPD7150	Approved
0.7654	Intermediate Similarity	NPD7152	Approved
0.7654	Intermediate Similarity	NPD7151	Approved
0.7653	Intermediate Similarity	NPD5141	Approved
0.764	Intermediate Similarity	NPD4690	Approved
0.764	Intermediate Similarity	NPD7334	Approved
0.764	Intermediate Similarity	NPD5690	Phase 2
0.764	Intermediate Similarity	NPD4693	Phase 3
0.764	Intermediate Similarity	NPD4694	Approved
0.764	Intermediate Similarity	NPD6409	Approved
0.764	Intermediate Similarity	NPD5205	Approved
0.764	Intermediate Similarity	NPD4688	Approved
0.764	Intermediate Similarity	NPD4138	Approved
0.764	Intermediate Similarity	NPD5330	Approved
0.764	Intermediate Similarity	NPD7146	Approved
0.764	Intermediate Similarity	NPD6684	Approved
0.764	Intermediate Similarity	NPD7521	Approved
0.764	Intermediate Similarity	NPD4689	Approved
0.764	Intermediate Similarity	NPD5280	Approved
0.7625	Intermediate Similarity	NPD6923	Approved
0.7625	Intermediate Similarity	NPD6922	Approved
0.7609	Intermediate Similarity	NPD7515	Phase 2
0.76	Intermediate Similarity	NPD6881	Approved
0.76	Intermediate Similarity	NPD7320	Approved
0.76	Intermediate Similarity	NPD6899	Approved
0.7579	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD6083	Phase 2
0.7576	Intermediate Similarity	NPD4767	Approved
0.7576	Intermediate Similarity	NPD4768	Approved
0.7558	Intermediate Similarity	NPD7525	Registered
0.7553	Intermediate Similarity	NPD4629	Approved
0.7553	Intermediate Similarity	NPD5210	Approved
0.7531	Intermediate Similarity	NPD7143	Approved
0.7531	Intermediate Similarity	NPD7144	Approved
0.7529	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7529	Intermediate Similarity	NPD3617	Approved
0.7525	Intermediate Similarity	NPD6372	Approved
0.7525	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD5701	Approved
0.75	Intermediate Similarity	NPD5697	Approved
0.7473	Intermediate Similarity	NPD5737	Approved
0.7473	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD6672	Approved
0.7473	Intermediate Similarity	NPD6903	Approved
0.7471	Intermediate Similarity	NPD4692	Approved
0.7471	Intermediate Similarity	NPD4139	Approved
0.7451	Intermediate Similarity	NPD7102	Approved
0.7451	Intermediate Similarity	NPD6883	Approved
0.7451	Intermediate Similarity	NPD7290	Approved
0.7442	Intermediate Similarity	NPD6929	Approved
0.7439	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD4729	Approved
0.7426	Intermediate Similarity	NPD5128	Approved
0.7426	Intermediate Similarity	NPD4730	Approved
0.7426	Intermediate Similarity	NPD5168	Approved
0.7426	Intermediate Similarity	NPD6011	Approved
0.7419	Intermediate Similarity	NPD6411	Approved
0.7379	Intermediate Similarity	NPD6650	Approved
0.7379	Intermediate Similarity	NPD6617	Approved
0.7379	Intermediate Similarity	NPD6869	Approved
0.7379	Intermediate Similarity	NPD8130	Phase 1
0.7379	Intermediate Similarity	NPD6649	Approved
0.7379	Intermediate Similarity	NPD6847	Approved
0.7379	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5695	Phase 3
0.7356	Intermediate Similarity	NPD5368	Approved
0.7356	Intermediate Similarity	NPD6930	Phase 2
0.7356	Intermediate Similarity	NPD6931	Approved
0.7356	Intermediate Similarity	NPD4695	Discontinued
0.7353	Intermediate Similarity	NPD6012	Approved
0.7353	Intermediate Similarity	NPD6014	Approved
0.7353	Intermediate Similarity	NPD6013	Approved
0.7342	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD4747	Approved
0.7308	Intermediate Similarity	NPD6882	Approved
0.7308	Intermediate Similarity	NPD8297	Approved
0.7283	Intermediate Similarity	NPD4518	Approved
0.7282	Intermediate Similarity	NPD5248	Approved
0.7282	Intermediate Similarity	NPD4634	Approved
0.7282	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD5249	Phase 3
0.7282	Intermediate Similarity	NPD5169	Approved
0.7282	Intermediate Similarity	NPD5247	Approved
0.7282	Intermediate Similarity	NPD5250	Approved
0.7282	Intermediate Similarity	NPD5251	Approved
0.7282	Intermediate Similarity	NPD5135	Approved
0.7263	Intermediate Similarity	NPD7748	Approved
0.7262	Intermediate Similarity	NPD5733	Approved
0.7262	Intermediate Similarity	NPD4785	Approved
0.7262	Intermediate Similarity	NPD4784	Approved
0.7253	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD6098	Approved
0.725	Intermediate Similarity	NPD7331	Phase 2
0.7241	Intermediate Similarity	NPD4195	Approved
0.7234	Intermediate Similarity	NPD5284	Approved
0.7234	Intermediate Similarity	NPD5281	Approved
0.7229	Intermediate Similarity	NPD4243	Approved
0.7212	Intermediate Similarity	NPD5215	Approved
0.7212	Intermediate Similarity	NPD5127	Approved
0.7212	Intermediate Similarity	NPD5216	Approved
0.7212	Intermediate Similarity	NPD5217	Approved
0.7209	Intermediate Similarity	NPD6932	Approved
0.7209	Intermediate Similarity	NPD6925	Approved
0.7209	Intermediate Similarity	NPD5776	Phase 2
0.7204	Intermediate Similarity	NPD6101	Approved
0.7204	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7195	Intermediate Similarity	NPD4137	Phase 3
0.7195	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6435	Approved
0.7176	Intermediate Similarity	NPD3703	Phase 2
0.7174	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD4748	Discontinued
0.7159	Intermediate Similarity	NPD7509	Discontinued
0.7143	Intermediate Similarity	NPD5696	Approved
0.7128	Intermediate Similarity	NPD4096	Approved
0.7126	Intermediate Similarity	NPD7145	Approved
0.7125	Intermediate Similarity	NPD7341	Phase 2
0.7111	Intermediate Similarity	NPD6695	Phase 3
0.7111	Intermediate Similarity	NPD5362	Discontinued
0.7108	Intermediate Similarity	NPD4245	Approved
0.7108	Intermediate Similarity	NPD4691	Approved
0.7108	Intermediate Similarity	NPD4789	Approved
0.7108	Intermediate Similarity	NPD4244	Approved
0.7103	Intermediate Similarity	NPD6868	Approved
0.7079	Intermediate Similarity	NPD5369	Approved
0.7075	Intermediate Similarity	NPD4632	Approved
0.7073	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7065	Intermediate Similarity	NPD4623	Approved
0.7065	Intermediate Similarity	NPD4519	Discontinued
0.7065	Intermediate Similarity	NPD5786	Approved
0.7059	Intermediate Similarity	NPD6008	Approved
0.7059	Intermediate Similarity	NPD4687	Approved
0.7059	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD8035	Phase 2
0.7053	Intermediate Similarity	NPD8034	Phase 2
0.7045	Intermediate Similarity	NPD6683	Phase 2
0.7045	Intermediate Similarity	NPD7645	Phase 2
0.7041	Intermediate Similarity	NPD7902	Approved
0.7033	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD5276	Approved
0.7021	Intermediate Similarity	NPD6673	Approved
0.7021	Intermediate Similarity	NPD6080	Approved
0.7021	Intermediate Similarity	NPD6904	Approved
0.7009	Intermediate Similarity	NPD5167	Approved
0.7	Intermediate Similarity	NPD4269	Approved
0.7	Intermediate Similarity	NPD4270	Approved
0.699	Remote Similarity	NPD6412	Phase 2
0.6988	Remote Similarity	NPD3698	Phase 2
0.6979	Remote Similarity	NPD5133	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