NPASS Compound

Structure

NPC184663 OpenBabel07101718202D 30 33 0 0 1 0 0 0 0 0999 V2000 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 -3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 -3.8660 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 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 -1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 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 1.5000 0.0000 C 0 0 0 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 2.5981 0.5000 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 1 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 1 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 3.4641 -0.0000 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 16 1 0 0 0 0 2 23 1 0 0 0 0 3 23 1 0 0 0 0 6 10 1 0 0 0 0 6 11 1 0 0 0 0 7 8 1 0 0 0 0 7 17 2 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 19 1 0 0 0 0 10 23 1 0 0 0 0 11 26 1 0 0 0 0 12 24 1 0 0 0 0 13 21 1 0 0 0 0 13 22 1 0 0 0 0 14 18 1 0 0 0 0 14 27 2 0 0 0 0 15 28 1 0 0 0 0 16 17 1 0 0 0 0 16 29 2 0 0 0 0 17 18 1 0 0 0 0 18 25 1 1 0 0 0 19 23 1 0 0 0 0 19 26 1 1 0 0 0 20 24 1 1 0 0 0 20 25 1 0 0 0 0 21 24 1 1 0 0 0 21 26 1 0 0 0 0 22 25 1 0 0 0 0 22 30 2 0 0 0 0 24 4 1 1 0 0 0 25 5 1 1 0 0 0 26 15 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	414.28
Volume:	448.641
LogP:	2.731
LogD:	2.92
LogS:	-4.038
# Rotatable Bonds:	3
TPSA:	71.44
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.689
Synthetic Accessibility Score:	4.98
Fsp3:	0.808
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.787
MDCK Permeability:	1.6733472875785083e-05
Pgp-inhibitor:	0.974
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.771
30% Bioavailability (F30%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.888
Plasma Protein Binding (PPB):	59.61749267578125%
Volume Distribution (VD):	1.647
Pgp-substrate:	38.023780822753906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.016
CYP1A2-substrate:	0.14
CYP2C19-inhibitor:	0.026
CYP2C19-substrate:	0.607
CYP2C9-inhibitor:	0.039
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.119
CYP3A4-inhibitor:	0.737
CYP3A4-substrate:	0.446

ADMET: Excretion

Clearance (CL):	8.346
Half-life (T1/2):	0.305

ADMET: Toxicity

hERG Blockers:	0.009
Human Hepatotoxicity (H-HT):	0.215
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.033
Rat Oral Acute Toxicity:	0.748
Maximum Recommended Daily Dose:	0.934
Skin Sensitization:	0.96
Carcinogencity:	0.556
Eye Corrosion:	0.961
Eye Irritation:	0.903
Respiratory Toxicity:	0.987

Download Data

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

Natural Product: NPC184663

Natural Product ID:	NPC184663
*Common Name:**	22-Hydroxy-24-Methyl-12,24-Dioxoscalar-16-En-25-Al
IUPAC Name:	(1S,4aS,4bR,6aS,10aR,10bS,12aS)-2-acetyl-10a-(hydroxymethyl)-4b,7,7,12a-tetramethyl-12-oxo-4,4a,5,6,6a,8,9,10,10b,11-decahydro-1H-chrysene-1-carbaldehyde
Synonyms:
Standard InCHIKey:	DTBKRPGPPWHXPW-HMEQYENBSA-N
Standard InCHI:	InChI=1S/C26H38O4/c1-16(29)17-7-8-20-24(4)12-9-19-23(2,3)10-6-11-26(19,15-28)21(24)13-22(30)25(20,5)18(17)14-27/h7,14,18-21,28H,6,8-13,15H2,1-5H3/t18-,19-,20-,21-,24-,25+,26+/m0/s1
SMILES:	CC(=O)C1=CC[C@H]2[C@]3(C)CC[C@H]4C(C)(C)CCC[C@]4(CO)[C@H]3CC(=O)[C@]2(C)[C@H]1C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1083495
PubChem CID:	23424966
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002883] Scalarane sesterterpenoids

*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
NPO33257	lendenfeldia sp.	Species	Thorectidae	Eukaryota	n.a.	Indonesian	n.a.	PMID[17958396]
NPO33257	lendenfeldia sp.	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[18989978]

☑ 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	14

Activity Type	# Activity
Cell Line	8
PROTEIN FAMILY	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT82	Cell Line	MDA-MB-231	Homo sapiens	IC50	=	300.0	nM	PMID[498369]
NPT83	Cell Line	MCF7	Homo sapiens	IC50	=	600.0	nM	PMID[498369]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	800.0	nM	PMID[498369]
NPT306	Cell Line	PC-3	Homo sapiens	IC50	=	1100.0	nM	PMID[498369]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	1200.0	nM	PMID[498369]
NPT396	Cell Line	T47D	Homo sapiens	IC50	=	1800.0	nM	PMID[498369]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	200.0	nM	PMID[498369]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	500.0	nM	PMID[498369]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	900.0	nM	PMID[498369]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	1000.0	nM	PMID[498369]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	=	2600.0	nM	PMID[498369]
NPT21802	PROTEIN FAMILY	Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha	Homo sapiens	IC50	>	10000.0	nM	PMID[498369]

☑ 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 NPC184663 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	195
0.1-0.2	1347
0.2-0.3	5725
0.3-0.4	14569
0.4-0.5	9033
0.5-0.6	6165
0.6-0.7	4310
0.7-0.8	1251
0.8-0.85	89
0.85-0.9	9
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9535	High Similarity	NPC230064
0.9277	High Similarity	NPC307258
0.908	High Similarity	NPC469546
0.8901	High Similarity	NPC469545
0.8901	High Similarity	NPC5532
0.8901	High Similarity	NPC61369
0.8864	High Similarity	NPC477973
0.875	High Similarity	NPC474925
0.875	High Similarity	NPC206060
0.8736	High Similarity	NPC158393
0.869	High Similarity	NPC2482
0.8675	High Similarity	NPC115515
0.8636	High Similarity	NPC93778
0.8588	High Similarity	NPC3915
0.8506	High Similarity	NPC476412
0.8488	Intermediate Similarity	NPC310989
0.8409	Intermediate Similarity	NPC469948
0.8372	Intermediate Similarity	NPC278459
0.8372	Intermediate Similarity	NPC116797
0.8372	Intermediate Similarity	NPC121984
0.8372	Intermediate Similarity	NPC90055
0.8372	Intermediate Similarity	NPC471898
0.837	Intermediate Similarity	NPC151722
0.8352	Intermediate Similarity	NPC252737
0.8352	Intermediate Similarity	NPC85173
0.8351	Intermediate Similarity	NPC95585
0.8351	Intermediate Similarity	NPC282233
0.8333	Intermediate Similarity	NPC474474
0.8333	Intermediate Similarity	NPC470524
0.8333	Intermediate Similarity	NPC472802
0.8315	Intermediate Similarity	NPC477579
0.8315	Intermediate Similarity	NPC95594
0.8315	Intermediate Similarity	NPC235341
0.8295	Intermediate Similarity	NPC180834
0.8295	Intermediate Similarity	NPC214043
0.8295	Intermediate Similarity	NPC470812
0.8295	Intermediate Similarity	NPC85774
0.8295	Intermediate Similarity	NPC96095
0.828	Intermediate Similarity	NPC23170
0.828	Intermediate Similarity	NPC471207
0.8276	Intermediate Similarity	NPC103486
0.8276	Intermediate Similarity	NPC302661
0.8276	Intermediate Similarity	NPC238991
0.8261	Intermediate Similarity	NPC272746
0.8261	Intermediate Similarity	NPC4036
0.8261	Intermediate Similarity	NPC233455
0.8261	Intermediate Similarity	NPC145067
0.8261	Intermediate Similarity	NPC158030
0.8261	Intermediate Similarity	NPC65120
0.8256	Intermediate Similarity	NPC472478
0.8242	Intermediate Similarity	NPC472983
0.8242	Intermediate Similarity	NPC477943
0.8235	Intermediate Similarity	NPC62336
0.8222	Intermediate Similarity	NPC158141
0.8222	Intermediate Similarity	NPC476409
0.8222	Intermediate Similarity	NPC173089
0.8222	Intermediate Similarity	NPC470523
0.8202	Intermediate Similarity	NPC474537
0.8202	Intermediate Similarity	NPC2709
0.8202	Intermediate Similarity	NPC133954
0.8202	Intermediate Similarity	NPC274724
0.8202	Intermediate Similarity	NPC476426
0.8193	Intermediate Similarity	NPC211641
0.8191	Intermediate Similarity	NPC274417
0.8191	Intermediate Similarity	NPC139570
0.8182	Intermediate Similarity	NPC53733
0.8182	Intermediate Similarity	NPC175410
0.8182	Intermediate Similarity	NPC102197
0.8172	Intermediate Similarity	NPC295643
0.8172	Intermediate Similarity	NPC474807
0.8172	Intermediate Similarity	NPC272075
0.8172	Intermediate Similarity	NPC214756
0.8161	Intermediate Similarity	NPC473217
0.8161	Intermediate Similarity	NPC221647
0.8161	Intermediate Similarity	NPC189237
0.8152	Intermediate Similarity	NPC191684
0.8152	Intermediate Similarity	NPC476437
0.8152	Intermediate Similarity	NPC476369
0.8132	Intermediate Similarity	NPC474511
0.8132	Intermediate Similarity	NPC1753
0.8125	Intermediate Similarity	NPC471966
0.8125	Intermediate Similarity	NPC194196
0.8111	Intermediate Similarity	NPC474733
0.8111	Intermediate Similarity	NPC145879
0.8111	Intermediate Similarity	NPC475862
0.8111	Intermediate Similarity	NPC474778
0.8111	Intermediate Similarity	NPC31564
0.8111	Intermediate Similarity	NPC474732
0.8111	Intermediate Similarity	NPC327115
0.8111	Intermediate Similarity	NPC213412
0.8111	Intermediate Similarity	NPC74363
0.8111	Intermediate Similarity	NPC324063
0.8105	Intermediate Similarity	NPC192428
0.8105	Intermediate Similarity	NPC471039
0.8105	Intermediate Similarity	NPC473158
0.8105	Intermediate Similarity	NPC473164
0.809	Intermediate Similarity	NPC227064
0.809	Intermediate Similarity	NPC473246
0.809	Intermediate Similarity	NPC321187
0.809	Intermediate Similarity	NPC227132
0.809	Intermediate Similarity	NPC329043
0.809	Intermediate Similarity	NPC237712
0.809	Intermediate Similarity	NPC58841
0.809	Intermediate Similarity	NPC161423
0.8085	Intermediate Similarity	NPC269729
0.8068	Intermediate Similarity	NPC212083
0.8065	Intermediate Similarity	NPC99380
0.8065	Intermediate Similarity	NPC472978
0.8046	Intermediate Similarity	NPC476809
0.8046	Intermediate Similarity	NPC37038
0.8046	Intermediate Similarity	NPC104545
0.8043	Intermediate Similarity	NPC31985
0.8043	Intermediate Similarity	NPC472973
0.8043	Intermediate Similarity	NPC186688
0.8043	Intermediate Similarity	NPC281524
0.8043	Intermediate Similarity	NPC1015
0.8043	Intermediate Similarity	NPC69627
0.8023	Intermediate Similarity	NPC59436
0.8023	Intermediate Similarity	NPC280654
0.8023	Intermediate Similarity	NPC110094
0.8023	Intermediate Similarity	NPC260385
0.8022	Intermediate Similarity	NPC475740
0.8022	Intermediate Similarity	NPC73064
0.8022	Intermediate Similarity	NPC58063
0.8021	Intermediate Similarity	NPC473456
0.8	Intermediate Similarity	NPC148523
0.8	Intermediate Similarity	NPC470525
0.8	Intermediate Similarity	NPC6185
0.8	Intermediate Similarity	NPC469993
0.8	Intermediate Similarity	NPC139459
0.8	Intermediate Similarity	NPC263582
0.8	Intermediate Similarity	NPC470574
0.8	Intermediate Similarity	NPC241512
0.7979	Intermediate Similarity	NPC211230
0.7979	Intermediate Similarity	NPC476416
0.7979	Intermediate Similarity	NPC250575
0.7979	Intermediate Similarity	NPC298554
0.7979	Intermediate Similarity	NPC233118
0.7978	Intermediate Similarity	NPC470165
0.7976	Intermediate Similarity	NPC219232
0.7976	Intermediate Similarity	NPC128346
0.7957	Intermediate Similarity	NPC291028
0.7957	Intermediate Similarity	NPC46441
0.7957	Intermediate Similarity	NPC183283
0.7957	Intermediate Similarity	NPC159748
0.7957	Intermediate Similarity	NPC126993
0.7957	Intermediate Similarity	NPC101651
0.7957	Intermediate Similarity	NPC193750
0.7957	Intermediate Similarity	NPC129913
0.7957	Intermediate Similarity	NPC328141
0.7955	Intermediate Similarity	NPC274050
0.7955	Intermediate Similarity	NPC267691
0.7955	Intermediate Similarity	NPC162632
0.7955	Intermediate Similarity	NPC44963
0.7955	Intermediate Similarity	NPC263272
0.7955	Intermediate Similarity	NPC55869
0.7955	Intermediate Similarity	NPC472684
0.7952	Intermediate Similarity	NPC474562
0.7938	Intermediate Similarity	NPC147954
0.7935	Intermediate Similarity	NPC158778
0.7935	Intermediate Similarity	NPC182797
0.7935	Intermediate Similarity	NPC328539
0.7935	Intermediate Similarity	NPC52169
0.7935	Intermediate Similarity	NPC230387
0.7935	Intermediate Similarity	NPC473229
0.7931	Intermediate Similarity	NPC472490
0.7931	Intermediate Similarity	NPC152061
0.7931	Intermediate Similarity	NPC476812
0.7931	Intermediate Similarity	NPC231431
0.7931	Intermediate Similarity	NPC474113
0.7931	Intermediate Similarity	NPC199595
0.7917	Intermediate Similarity	NPC472806
0.7917	Intermediate Similarity	NPC472941
0.7917	Intermediate Similarity	NPC456
0.7917	Intermediate Similarity	NPC167193
0.7917	Intermediate Similarity	NPC98874
0.7912	Intermediate Similarity	NPC229717
0.7912	Intermediate Similarity	NPC94666
0.7912	Intermediate Similarity	NPC34190
0.7907	Intermediate Similarity	NPC149249
0.7907	Intermediate Similarity	NPC197659
0.7907	Intermediate Similarity	NPC106078
0.7907	Intermediate Similarity	NPC107039
0.7907	Intermediate Similarity	NPC471897
0.7907	Intermediate Similarity	NPC165711
0.7907	Intermediate Similarity	NPC471899
0.7907	Intermediate Similarity	NPC476811
0.7895	Intermediate Similarity	NPC472977
0.7895	Intermediate Similarity	NPC473172
0.7895	Intermediate Similarity	NPC222047
0.7895	Intermediate Similarity	NPC476415
0.7895	Intermediate Similarity	NPC471040
0.7895	Intermediate Similarity	NPC74751
0.7895	Intermediate Similarity	NPC474529
0.7895	Intermediate Similarity	NPC472976
0.7895	Intermediate Similarity	NPC474882
0.7895	Intermediate Similarity	NPC209868
0.7889	Intermediate Similarity	NPC59453
0.7889	Intermediate Similarity	NPC221758
0.7889	Intermediate Similarity	NPC472265

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 NPC184663 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	178
0.1-0.2	1720
0.2-0.3	4062
0.3-0.4	2258
0.4-0.5	529
0.5-0.6	163
0.6-0.7	166
0.7-0.8	73
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8261	Intermediate Similarity	NPD7515	Phase 2
0.8105	Intermediate Similarity	NPD4697	Phase 3
0.809	Intermediate Similarity	NPD3666	Approved
0.809	Intermediate Similarity	NPD3133	Approved
0.809	Intermediate Similarity	NPD3665	Phase 1
0.8065	Intermediate Similarity	NPD6079	Approved
0.8046	Intermediate Similarity	NPD4695	Discontinued
0.8043	Intermediate Similarity	NPD5328	Approved
0.8	Intermediate Similarity	NPD4629	Approved
0.8	Intermediate Similarity	NPD5210	Approved
0.7917	Intermediate Similarity	NPD7614	Phase 1
0.7912	Intermediate Similarity	NPD3618	Phase 1
0.7895	Intermediate Similarity	NPD7748	Approved
0.7889	Intermediate Similarity	NPD4786	Approved
0.7865	Intermediate Similarity	NPD3667	Approved
0.7849	Intermediate Similarity	NPD4753	Phase 2
0.7835	Intermediate Similarity	NPD7902	Approved
0.7732	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7732	Intermediate Similarity	NPD5222	Approved
0.7732	Intermediate Similarity	NPD5221	Approved
0.7667	Intermediate Similarity	NPD4221	Approved
0.7667	Intermediate Similarity	NPD4223	Phase 3
0.766	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7653	Intermediate Similarity	NPD5173	Approved
0.7609	Intermediate Similarity	NPD5329	Approved
0.7582	Intermediate Similarity	NPD4788	Approved
0.7553	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD7732	Phase 3
0.7527	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5279	Phase 3
0.7526	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7900	Approved
0.75	Intermediate Similarity	NPD4197	Approved
0.75	Intermediate Similarity	NPD5286	Approved
0.75	Intermediate Similarity	NPD4696	Approved
0.75	Intermediate Similarity	NPD5285	Approved
0.7475	Intermediate Similarity	NPD4755	Approved
0.7475	Intermediate Similarity	NPD6084	Phase 2
0.7475	Intermediate Similarity	NPD6083	Phase 2
0.7426	Intermediate Similarity	NPD5223	Approved
0.7423	Intermediate Similarity	NPD4202	Approved
0.7423	Intermediate Similarity	NPD6399	Phase 3
0.7416	Intermediate Similarity	NPD3617	Approved
0.74	Intermediate Similarity	NPD5696	Approved
0.7368	Intermediate Similarity	NPD6672	Approved
0.7368	Intermediate Similarity	NPD5737	Approved
0.7353	Intermediate Similarity	NPD5224	Approved
0.7353	Intermediate Similarity	NPD5211	Phase 2
0.7353	Intermediate Similarity	NPD5225	Approved
0.7353	Intermediate Similarity	NPD5226	Approved
0.7353	Intermediate Similarity	NPD4633	Approved
0.734	Intermediate Similarity	NPD6684	Approved
0.734	Intermediate Similarity	NPD5690	Phase 2
0.734	Intermediate Similarity	NPD4519	Discontinued
0.734	Intermediate Similarity	NPD6409	Approved
0.734	Intermediate Similarity	NPD4693	Phase 3
0.734	Intermediate Similarity	NPD7521	Approved
0.734	Intermediate Similarity	NPD5330	Approved
0.734	Intermediate Similarity	NPD7334	Approved
0.734	Intermediate Similarity	NPD4138	Approved
0.734	Intermediate Similarity	NPD4623	Approved
0.734	Intermediate Similarity	NPD4689	Approved
0.734	Intermediate Similarity	NPD4690	Approved
0.734	Intermediate Similarity	NPD5205	Approved
0.734	Intermediate Similarity	NPD4688	Approved
0.734	Intermediate Similarity	NPD7146	Approved
0.7327	Intermediate Similarity	NPD4700	Approved
0.7312	Intermediate Similarity	NPD3668	Phase 3
0.7282	Intermediate Similarity	NPD5175	Approved
0.7282	Intermediate Similarity	NPD5174	Approved
0.7263	Intermediate Similarity	NPD3573	Approved
0.7212	Intermediate Similarity	NPD5141	Approved
0.7209	Intermediate Similarity	NPD4691	Approved
0.7188	Intermediate Similarity	NPD6903	Approved
0.717	Intermediate Similarity	NPD6881	Approved
0.717	Intermediate Similarity	NPD6899	Approved
0.7158	Intermediate Similarity	NPD4694	Approved
0.7158	Intermediate Similarity	NPD5280	Approved
0.7143	Intermediate Similarity	NPD6402	Approved
0.7143	Intermediate Similarity	NPD7128	Approved
0.7143	Intermediate Similarity	NPD4195	Approved
0.7143	Intermediate Similarity	NPD5739	Approved
0.7143	Intermediate Similarity	NPD6675	Approved
0.7143	Intermediate Similarity	NPD7645	Phase 2
0.713	Intermediate Similarity	NPD6650	Approved
0.713	Intermediate Similarity	NPD6649	Approved
0.7115	Intermediate Similarity	NPD4754	Approved
0.7103	Intermediate Similarity	NPD6372	Approved
0.7103	Intermediate Similarity	NPD6373	Approved
0.71	Intermediate Similarity	NPD5695	Phase 3
0.7093	Intermediate Similarity	NPD4137	Phase 3
0.7075	Intermediate Similarity	NPD5697	Approved
0.7075	Intermediate Similarity	NPD6412	Phase 2
0.7053	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD7290	Approved
0.7037	Intermediate Similarity	NPD6883	Approved
0.7037	Intermediate Similarity	NPD7102	Approved
0.7019	Intermediate Similarity	NPD5091	Approved
0.7011	Intermediate Similarity	NPD4747	Approved
0.7009	Intermediate Similarity	NPD4729	Approved
0.7009	Intermediate Similarity	NPD4730	Approved
0.7009	Intermediate Similarity	NPD6011	Approved
0.7009	Intermediate Similarity	NPD5128	Approved
0.7009	Intermediate Similarity	NPD5168	Approved
0.7009	Intermediate Similarity	NPD7320	Approved
0.6981	Remote Similarity	NPD4768	Approved
0.6981	Remote Similarity	NPD4767	Approved
0.6972	Remote Similarity	NPD8130	Phase 1
0.6972	Remote Similarity	NPD6617	Approved
0.6972	Remote Similarity	NPD6869	Approved
0.6972	Remote Similarity	NPD6847	Approved
0.697	Remote Similarity	NPD5281	Approved
0.697	Remote Similarity	NPD5284	Approved
0.6966	Remote Similarity	NPD4058	Approved
0.6944	Remote Similarity	NPD6012	Approved
0.6944	Remote Similarity	NPD6013	Approved
0.6944	Remote Similarity	NPD6014	Approved
0.6941	Remote Similarity	NPD7331	Phase 2
0.6939	Remote Similarity	NPD6904	Approved
0.6939	Remote Similarity	NPD6080	Approved
0.6939	Remote Similarity	NPD6673	Approved
0.6916	Remote Similarity	NPD5701	Approved
0.6915	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD8297	Approved
0.6909	Remote Similarity	NPD6882	Approved
0.6893	Remote Similarity	NPD7638	Approved
0.6889	Remote Similarity	NPD6942	Approved
0.6889	Remote Similarity	NPD7339	Approved
0.6882	Remote Similarity	NPD7525	Registered
0.6881	Remote Similarity	NPD4634	Approved
0.6881	Remote Similarity	NPD5250	Approved
0.6881	Remote Similarity	NPD5251	Approved
0.6881	Remote Similarity	NPD5247	Approved
0.6881	Remote Similarity	NPD5169	Approved
0.6881	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD5135	Approved
0.6881	Remote Similarity	NPD5249	Phase 3
0.6881	Remote Similarity	NPD5248	Approved
0.6827	Remote Similarity	NPD7640	Approved
0.6827	Remote Similarity	NPD7639	Approved
0.6824	Remote Similarity	NPD7341	Phase 2
0.6818	Remote Similarity	NPD5127	Approved
0.6818	Remote Similarity	NPD5215	Approved
0.6818	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5217	Approved
0.6818	Remote Similarity	NPD5216	Approved
0.6813	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6809	Remote Similarity	NPD8028	Phase 2
0.68	Remote Similarity	NPD8034	Phase 2
0.68	Remote Similarity	NPD8035	Phase 2
0.68	Remote Similarity	NPD6411	Approved
0.6778	Remote Similarity	NPD5733	Approved
0.6765	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6868	Approved
0.6702	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.67	Remote Similarity	NPD4096	Approved
0.6696	Remote Similarity	NPD4632	Approved
0.6667	Remote Similarity	NPD5208	Approved
0.6667	Remote Similarity	NPD7115	Discovery
0.6637	Remote Similarity	NPD5167	Approved
0.6634	Remote Similarity	NPD5693	Phase 1
0.6634	Remote Similarity	NPD6050	Approved
0.6633	Remote Similarity	NPD6098	Approved
0.6632	Remote Similarity	NPD4139	Approved
0.6632	Remote Similarity	NPD4692	Approved
0.6629	Remote Similarity	NPD4789	Approved
0.6629	Remote Similarity	NPD4245	Approved
0.6629	Remote Similarity	NPD4244	Approved
0.6609	Remote Similarity	NPD6335	Approved
0.66	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.66	Remote Similarity	NPD6101	Approved
0.6593	Remote Similarity	NPD4687	Approved
0.6591	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6274	Approved
0.6569	Remote Similarity	NPD5133	Approved
0.6556	Remote Similarity	NPD6081	Approved
0.6556	Remote Similarity	NPD5276	Approved
0.6556	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4243	Approved
0.6552	Remote Similarity	NPD7101	Approved
0.6552	Remote Similarity	NPD7100	Approved
0.6545	Remote Similarity	NPD6686	Approved
0.6535	Remote Similarity	NPD5692	Phase 3
0.6531	Remote Similarity	NPD1696	Phase 3
0.6522	Remote Similarity	NPD6009	Approved
0.6522	Remote Similarity	NPD6317	Approved
0.6517	Remote Similarity	NPD3698	Phase 2
0.6517	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.65	Remote Similarity	NPD4518	Approved
0.6496	Remote Similarity	NPD6054	Approved
0.6471	Remote Similarity	NPD8328	Phase 3
0.6471	Remote Similarity	NPD5694	Approved
0.6466	Remote Similarity	NPD6313	Approved
0.6466	Remote Similarity	NPD6314	Approved
0.6455	Remote Similarity	NPD6614	Approved
0.6437	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5290	Discontinued
0.6413	Remote Similarity	NPD4784	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