NPASS Compound

Structure

NPC206060 OpenBabel07101719252D 26 29 0 0 1 0 0 0 0 0999 V2000 -4.1712 3.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5402 3.3827 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 -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 -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 -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 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 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 -2.5981 1.5000 0.0000 C 0 0 2 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 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 21 1 0 0 0 0 2 21 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 16 1 0 0 0 0 8 18 1 0 0 0 0 9 12 1 0 0 0 0 9 17 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 23 1 0 0 0 0 13 19 1 0 0 0 0 13 20 1 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 25 2 0 0 0 0 17 21 1 0 0 0 0 17 22 1 6 0 0 0 18 23 1 6 0 0 0 18 24 1 0 0 0 0 19 22 1 6 0 0 0 19 23 1 0 0 0 0 20 24 1 6 0 0 0 20 26 1 0 0 0 0 22 3 1 6 0 0 0 23 4 1 6 0 0 0 24 5 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	358.29
Volume:	401.742
LogP:	5.209
LogD:	4.32
LogS:	-5.41
# Rotatable Bonds:	1
TPSA:	37.3
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.625
Synthetic Accessibility Score:	4.765
Fsp3:	0.875
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.789
MDCK Permeability:	1.5244446331053041e-05
Pgp-inhibitor:	0.97
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.744
30% Bioavailability (F30%):	0.952

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.123
Plasma Protein Binding (PPB):	91.6625747680664%
Volume Distribution (VD):	1.041
Pgp-substrate:	4.836757659912109%

ADMET: Metabolism

CYP1A2-inhibitor:	0.081
CYP1A2-substrate:	0.245
CYP2C19-inhibitor:	0.185
CYP2C19-substrate:	0.825
CYP2C9-inhibitor:	0.351
CYP2C9-substrate:	0.508
CYP2D6-inhibitor:	0.193
CYP2D6-substrate:	0.723
CYP3A4-inhibitor:	0.721
CYP3A4-substrate:	0.339

ADMET: Excretion

Clearance (CL):	5.615
Half-life (T1/2):	0.133

ADMET: Toxicity

hERG Blockers:	0.23
Human Hepatotoxicity (H-HT):	0.553
Drug-inuced Liver Injury (DILI):	0.036
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.908
Skin Sensitization:	0.938
Carcinogencity:	0.211
Eye Corrosion:	0.976
Eye Irritation:	0.789
Respiratory Toxicity:	0.972

Download Data

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

Natural Product: NPC206060

Natural Product ID:	NPC206060
*Common Name:**	12-Deacetyl-Delta 17-Hyrtial
IUPAC Name:	(4aS,4bR,6aS,10aS,10bR,12R,12aR)-12-hydroxy-4b,7,7,10a,12a-pentamethyl-3,4,4a,5,6,6a,8,9,10,10b,11,12-dodecahydrochrysene-2-carbaldehyde
Synonyms:
Standard InCHIKey:	KSEAOAMBWFKBNK-CZRCWOFFSA-N
Standard InCHI:	InChI=1S/C24H38O2/c1-21(2)10-6-11-22(3)17(21)9-12-23(4)18-8-7-16(15-25)14-24(18,5)20(26)13-19(22)23/h14-15,17-20,26H,6-13H2,1-5H3/t17-,18-,19+,20+,22-,23-,24+/m0/s1
SMILES:	CC1(C)CCC[C@@]2(C)[C@H]1CC[C@@]1(C)[C@@H]3CCC(=C[C@@]3(C)[C@@H](C[C@H]21)O)C=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL518934
PubChem CID:	10522424
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
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Okinawan	n.a.	PMID[11076554]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	red sea	n.a.	PMID[16180827]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	Red Sea	n.a.	PMID[17190441]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[3572416]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[8778242]
NPO5239	Hyrtios erecta	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	PMID[9461648]
NPO5239	Hyrtios erecta	Species	Thorectidae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT91	Cell Line	KB	Homo sapiens	IC50	=	2.82	ug.mL-1	PMID[506726]

☑ 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 NPC206060 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	196
0.1-0.2	1267
0.2-0.3	4899
0.3-0.4	13469
0.4-0.5	10014
0.5-0.6	5904
0.6-0.7	4744
0.7-0.8	1793
0.8-0.85	325
0.85-0.9	74
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9524	High Similarity	NPC474925
0.9286	High Similarity	NPC95594
0.9286	High Similarity	NPC235341
0.9286	High Similarity	NPC477579
0.9157	High Similarity	NPC307258
0.908	High Similarity	NPC85173
0.907	High Similarity	NPC472802
0.9059	High Similarity	NPC158393
0.9	High Similarity	NPC469545
0.9	High Similarity	NPC5532
0.9	High Similarity	NPC61369
0.8989	High Similarity	NPC23170
0.8977	High Similarity	NPC272746
0.8953	High Similarity	NPC73064
0.8941	High Similarity	NPC133954
0.8864	High Similarity	NPC191684
0.8851	High Similarity	NPC181225
0.8851	High Similarity	NPC290690
0.8851	High Similarity	NPC473229
0.8851	High Similarity	NPC470629
0.8851	High Similarity	NPC17733
0.8851	High Similarity	NPC473242
0.8851	High Similarity	NPC474512
0.8837	High Similarity	NPC475862
0.8837	High Similarity	NPC213412
0.8837	High Similarity	NPC74363
0.8824	High Similarity	NPC180834
0.8804	High Similarity	NPC194196
0.8795	High Similarity	NPC2482
0.8778	High Similarity	NPC471207
0.8778	High Similarity	NPC209868
0.8764	High Similarity	NPC65120
0.8764	High Similarity	NPC145067
0.8764	High Similarity	NPC233455
0.8764	High Similarity	NPC158030
0.8764	High Similarity	NPC4036
0.875	High Similarity	NPC143232
0.875	High Similarity	NPC472983
0.875	High Similarity	NPC184663
0.875	High Similarity	NPC274330
0.875	High Similarity	NPC119416
0.875	High Similarity	NPC470588
0.875	High Similarity	NPC198664
0.8736	High Similarity	NPC18064
0.8736	High Similarity	NPC475740
0.8736	High Similarity	NPC130577
0.8736	High Similarity	NPC98442
0.8736	High Similarity	NPC171203
0.8736	High Similarity	NPC71507
0.8736	High Similarity	NPC142415
0.8736	High Similarity	NPC242468
0.8736	High Similarity	NPC51700
0.8736	High Similarity	NPC307426
0.8736	High Similarity	NPC293564
0.8736	High Similarity	NPC102683
0.8736	High Similarity	NPC88716
0.8736	High Similarity	NPC68160
0.8721	High Similarity	NPC470574
0.869	High Similarity	NPC473217
0.8675	High Similarity	NPC470429
0.8667	High Similarity	NPC298554
0.8667	High Similarity	NPC214756
0.8667	High Similarity	NPC272075
0.8667	High Similarity	NPC295643
0.8659	High Similarity	NPC470428
0.8652	High Similarity	NPC470589
0.8652	High Similarity	NPC126993
0.8652	High Similarity	NPC126369
0.8652	High Similarity	NPC111110
0.8652	High Similarity	NPC328141
0.8636	High Similarity	NPC246708
0.8636	High Similarity	NPC230387
0.8636	High Similarity	NPC471722
0.8636	High Similarity	NPC52169
0.8636	High Similarity	NPC40552
0.8636	High Similarity	NPC474677
0.8636	High Similarity	NPC182797
0.8621	High Similarity	NPC94755
0.8621	High Similarity	NPC72638
0.8621	High Similarity	NPC474778
0.8621	High Similarity	NPC145879
0.8621	High Similarity	NPC269396
0.8621	High Similarity	NPC31564
0.8621	High Similarity	NPC474732
0.8621	High Similarity	NPC98236
0.8621	High Similarity	NPC474733
0.8605	High Similarity	NPC470812
0.8602	High Similarity	NPC471966
0.8588	High Similarity	NPC48362
0.8588	High Similarity	NPC310989
0.8587	High Similarity	NPC473158
0.8571	High Similarity	NPC222047
0.8556	High Similarity	NPC187722
0.8556	High Similarity	NPC99380
0.8556	High Similarity	NPC301244
0.8554	High Similarity	NPC253561
0.8554	High Similarity	NPC476949
0.8554	High Similarity	NPC80088
0.8539	High Similarity	NPC474686
0.8539	High Similarity	NPC474972
0.8539	High Similarity	NPC161751
0.8539	High Similarity	NPC293048
0.8539	High Similarity	NPC290972
0.8539	High Similarity	NPC477973
0.8539	High Similarity	NPC1015
0.8539	High Similarity	NPC25906
0.8539	High Similarity	NPC64872
0.8539	High Similarity	NPC234346
0.8539	High Similarity	NPC472973
0.8539	High Similarity	NPC95246
0.8539	High Similarity	NPC127689
0.8539	High Similarity	NPC270768
0.8539	High Similarity	NPC31985
0.8539	High Similarity	NPC61543
0.8539	High Similarity	NPC225585
0.8539	High Similarity	NPC130520
0.8539	High Similarity	NPC69627
0.8539	High Similarity	NPC59263
0.8539	High Similarity	NPC121798
0.8539	High Similarity	NPC263393
0.8523	High Similarity	NPC89747
0.8523	High Similarity	NPC93778
0.8523	High Similarity	NPC58063
0.8495	Intermediate Similarity	NPC21728
0.8495	Intermediate Similarity	NPC187933
0.8478	Intermediate Similarity	NPC148523
0.8478	Intermediate Similarity	NPC139570
0.8471	Intermediate Similarity	NPC119229
0.8471	Intermediate Similarity	NPC121984
0.8471	Intermediate Similarity	NPC473420
0.8471	Intermediate Similarity	NPC3915
0.8462	Intermediate Similarity	NPC118519
0.8462	Intermediate Similarity	NPC202728
0.8462	Intermediate Similarity	NPC158059
0.8462	Intermediate Similarity	NPC12722
0.8462	Intermediate Similarity	NPC229281
0.8462	Intermediate Similarity	NPC474806
0.8462	Intermediate Similarity	NPC133579
0.8462	Intermediate Similarity	NPC211230
0.8444	Intermediate Similarity	NPC474728
0.8444	Intermediate Similarity	NPC120968
0.8444	Intermediate Similarity	NPC172361
0.8444	Intermediate Similarity	NPC48010
0.8444	Intermediate Similarity	NPC291028
0.8444	Intermediate Similarity	NPC18872
0.8444	Intermediate Similarity	NPC210037
0.8444	Intermediate Similarity	NPC290614
0.8444	Intermediate Similarity	NPC477872
0.8444	Intermediate Similarity	NPC130278
0.8444	Intermediate Similarity	NPC273621
0.8444	Intermediate Similarity	NPC7260
0.8444	Intermediate Similarity	NPC183283
0.8444	Intermediate Similarity	NPC86372
0.8444	Intermediate Similarity	NPC227467
0.8438	Intermediate Similarity	NPC282233
0.8438	Intermediate Similarity	NPC95585
0.8434	Intermediate Similarity	NPC197659
0.8427	Intermediate Similarity	NPC472739
0.8427	Intermediate Similarity	NPC158778
0.8427	Intermediate Similarity	NPC328539
0.8409	Intermediate Similarity	NPC72133
0.8409	Intermediate Similarity	NPC73038
0.8409	Intermediate Similarity	NPC472974
0.8409	Intermediate Similarity	NPC325594
0.8409	Intermediate Similarity	NPC472986
0.8409	Intermediate Similarity	NPC472985
0.8409	Intermediate Similarity	NPC94666
0.8409	Intermediate Similarity	NPC471737
0.8404	Intermediate Similarity	NPC478056
0.8391	Intermediate Similarity	NPC74595
0.8391	Intermediate Similarity	NPC171789
0.8391	Intermediate Similarity	NPC214043
0.8391	Intermediate Similarity	NPC472265
0.8391	Intermediate Similarity	NPC59453
0.8391	Intermediate Similarity	NPC85774
0.8391	Intermediate Similarity	NPC221758
0.8391	Intermediate Similarity	NPC264665
0.8387	Intermediate Similarity	NPC167193
0.8387	Intermediate Similarity	NPC472806
0.8387	Intermediate Similarity	NPC471039
0.8387	Intermediate Similarity	NPC98874
0.8372	Intermediate Similarity	NPC163236
0.8372	Intermediate Similarity	NPC151519
0.837	Intermediate Similarity	NPC80365
0.837	Intermediate Similarity	NPC196485
0.837	Intermediate Similarity	NPC114159
0.837	Intermediate Similarity	NPC474328
0.837	Intermediate Similarity	NPC191412
0.837	Intermediate Similarity	NPC472977
0.837	Intermediate Similarity	NPC159365
0.837	Intermediate Similarity	NPC472976
0.837	Intermediate Similarity	NPC74751
0.837	Intermediate Similarity	NPC6818
0.837	Intermediate Similarity	NPC245972
0.837	Intermediate Similarity	NPC269729
0.8353	Intermediate Similarity	NPC476809
0.8352	Intermediate Similarity	NPC77099
0.8352	Intermediate Similarity	NPC131872
0.8352	Intermediate Similarity	NPC60755
0.8352	Intermediate Similarity	NPC155120

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 NPC206060 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	181
0.1-0.2	1645
0.2-0.3	3868
0.3-0.4	2390
0.4-0.5	641
0.5-0.6	162
0.6-0.7	167
0.7-0.8	89
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8764	High Similarity	NPD7515	Phase 2
0.8621	High Similarity	NPD3618	Phase 1
0.8556	High Similarity	NPD6079	Approved
0.8539	High Similarity	NPD5328	Approved
0.8391	Intermediate Similarity	NPD4786	Approved
0.8372	Intermediate Similarity	NPD3667	Approved
0.837	Intermediate Similarity	NPD7748	Approved
0.8191	Intermediate Similarity	NPD4697	Phase 3
0.8182	Intermediate Similarity	NPD3133	Approved
0.8182	Intermediate Similarity	NPD3666	Approved
0.8182	Intermediate Similarity	NPD3665	Phase 1
0.8105	Intermediate Similarity	NPD7902	Approved
0.8065	Intermediate Similarity	NPD4202	Approved
0.8023	Intermediate Similarity	NPD7645	Phase 2
0.8	Intermediate Similarity	NPD5222	Approved
0.8	Intermediate Similarity	NPD5221	Approved
0.8	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7931	Intermediate Similarity	NPD4695	Discontinued
0.7917	Intermediate Similarity	NPD5173	Approved
0.7889	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7789	Intermediate Similarity	NPD7900	Approved
0.7789	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.7755	Intermediate Similarity	NPD5286	Approved
0.7755	Intermediate Similarity	NPD4696	Approved
0.7755	Intermediate Similarity	NPD5285	Approved
0.7732	Intermediate Similarity	NPD4755	Approved
0.7677	Intermediate Similarity	NPD5223	Approved
0.7634	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5279	Phase 3
0.76	Intermediate Similarity	NPD5225	Approved
0.76	Intermediate Similarity	NPD5211	Phase 2
0.76	Intermediate Similarity	NPD4633	Approved
0.76	Intermediate Similarity	NPD5224	Approved
0.76	Intermediate Similarity	NPD5226	Approved
0.7582	Intermediate Similarity	NPD3668	Phase 3
0.7576	Intermediate Similarity	NPD4700	Approved
0.7558	Intermediate Similarity	NPD6942	Approved
0.7558	Intermediate Similarity	NPD7339	Approved
0.7556	Intermediate Similarity	NPD4223	Phase 3
0.7556	Intermediate Similarity	NPD4221	Approved
0.7553	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7553	Intermediate Similarity	NPD4753	Phase 2
0.7528	Intermediate Similarity	NPD7525	Registered
0.7527	Intermediate Similarity	NPD3573	Approved
0.7525	Intermediate Similarity	NPD5175	Approved
0.7525	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD5329	Approved
0.75	Intermediate Similarity	NPD6399	Phase 3
0.7475	Intermediate Similarity	NPD7638	Approved
0.7473	Intermediate Similarity	NPD4788	Approved
0.7471	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7451	Intermediate Similarity	NPD5141	Approved
0.7419	Intermediate Similarity	NPD7334	Approved
0.7419	Intermediate Similarity	NPD6684	Approved
0.7419	Intermediate Similarity	NPD5330	Approved
0.7419	Intermediate Similarity	NPD6409	Approved
0.7419	Intermediate Similarity	NPD7146	Approved
0.7419	Intermediate Similarity	NPD7521	Approved
0.7404	Intermediate Similarity	NPD6899	Approved
0.7404	Intermediate Similarity	NPD6881	Approved
0.74	Intermediate Similarity	NPD7640	Approved
0.74	Intermediate Similarity	NPD7639	Approved
0.7391	Intermediate Similarity	NPD4197	Approved
0.7379	Intermediate Similarity	NPD7128	Approved
0.7379	Intermediate Similarity	NPD5739	Approved
0.7379	Intermediate Similarity	NPD6675	Approved
0.7379	Intermediate Similarity	NPD6402	Approved
0.7353	Intermediate Similarity	NPD4754	Approved
0.7347	Intermediate Similarity	NPD4629	Approved
0.7347	Intermediate Similarity	NPD5210	Approved
0.7308	Intermediate Similarity	NPD5697	Approved
0.7303	Intermediate Similarity	NPD3617	Approved
0.7264	Intermediate Similarity	NPD6883	Approved
0.7264	Intermediate Similarity	NPD7290	Approved
0.7264	Intermediate Similarity	NPD7102	Approved
0.7263	Intermediate Similarity	NPD6903	Approved
0.7238	Intermediate Similarity	NPD4729	Approved
0.7238	Intermediate Similarity	NPD6011	Approved
0.7238	Intermediate Similarity	NPD5128	Approved
0.7238	Intermediate Similarity	NPD7320	Approved
0.7238	Intermediate Similarity	NPD5168	Approved
0.7238	Intermediate Similarity	NPD4730	Approved
0.7234	Intermediate Similarity	NPD4689	Approved
0.7234	Intermediate Similarity	NPD4623	Approved
0.7234	Intermediate Similarity	NPD5205	Approved
0.7234	Intermediate Similarity	NPD4690	Approved
0.7234	Intermediate Similarity	NPD5690	Phase 2
0.7234	Intermediate Similarity	NPD4519	Discontinued
0.7234	Intermediate Similarity	NPD4693	Phase 3
0.7234	Intermediate Similarity	NPD4688	Approved
0.7234	Intermediate Similarity	NPD4138	Approved
0.7216	Intermediate Similarity	NPD8034	Phase 2
0.7216	Intermediate Similarity	NPD8035	Phase 2
0.7212	Intermediate Similarity	NPD4767	Approved
0.7212	Intermediate Similarity	NPD4768	Approved
0.72	Intermediate Similarity	NPD6083	Phase 2
0.72	Intermediate Similarity	NPD6084	Phase 2
0.7196	Intermediate Similarity	NPD6869	Approved
0.7196	Intermediate Similarity	NPD6617	Approved
0.7196	Intermediate Similarity	NPD6649	Approved
0.7196	Intermediate Similarity	NPD8130	Phase 1
0.7196	Intermediate Similarity	NPD6847	Approved
0.7196	Intermediate Similarity	NPD6650	Approved
0.7182	Intermediate Similarity	NPD7115	Discovery
0.717	Intermediate Similarity	NPD6373	Approved
0.717	Intermediate Similarity	NPD6372	Approved
0.717	Intermediate Similarity	NPD6013	Approved
0.717	Intermediate Similarity	NPD6014	Approved
0.717	Intermediate Similarity	NPD6012	Approved
0.7143	Intermediate Similarity	NPD8259	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5701	Approved
0.713	Intermediate Similarity	NPD8297	Approved
0.713	Intermediate Similarity	NPD6882	Approved
0.7103	Intermediate Similarity	NPD5247	Approved
0.7103	Intermediate Similarity	NPD5251	Approved
0.7103	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4634	Approved
0.7103	Intermediate Similarity	NPD5135	Approved
0.7103	Intermediate Similarity	NPD5248	Approved
0.7103	Intermediate Similarity	NPD5249	Phase 3
0.7103	Intermediate Similarity	NPD5250	Approved
0.7103	Intermediate Similarity	NPD5169	Approved
0.71	Intermediate Similarity	NPD7614	Phase 1
0.7093	Intermediate Similarity	NPD4691	Approved
0.7083	Intermediate Similarity	NPD5737	Approved
0.7083	Intermediate Similarity	NPD6672	Approved
0.7053	Intermediate Similarity	NPD5280	Approved
0.7053	Intermediate Similarity	NPD4694	Approved
0.7041	Intermediate Similarity	NPD6411	Approved
0.7037	Intermediate Similarity	NPD5215	Approved
0.7037	Intermediate Similarity	NPD5127	Approved
0.7037	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7037	Intermediate Similarity	NPD5217	Approved
0.7037	Intermediate Similarity	NPD5216	Approved
0.7033	Intermediate Similarity	NPD4195	Approved
0.7011	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7011	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6412	Phase 2
0.6977	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD4137	Phase 3
0.6961	Remote Similarity	NPD4225	Approved
0.6961	Remote Similarity	NPD5290	Discontinued
0.6937	Remote Similarity	NPD6868	Approved
0.6909	Remote Similarity	NPD4632	Approved
0.6897	Remote Similarity	NPD4747	Approved
0.6889	Remote Similarity	NPD6117	Approved
0.6854	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD6924	Approved
0.6854	Remote Similarity	NPD4058	Approved
0.6854	Remote Similarity	NPD6926	Approved
0.6847	Remote Similarity	NPD5167	Approved
0.6837	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6837	Remote Similarity	NPD6101	Approved
0.6832	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5695	Phase 3
0.6814	Remote Similarity	NPD6335	Approved
0.6813	Remote Similarity	NPD6116	Phase 1
0.6809	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5696	Approved
0.6786	Remote Similarity	NPD6274	Approved
0.6778	Remote Similarity	NPD8264	Approved
0.6778	Remote Similarity	NPD3703	Phase 2
0.6771	Remote Similarity	NPD1696	Phase 3
0.6771	Remote Similarity	NPD1694	Approved
0.6765	Remote Similarity	NPD7732	Phase 3
0.6762	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD7100	Approved
0.6754	Remote Similarity	NPD7101	Approved
0.6739	Remote Similarity	NPD6114	Approved
0.6739	Remote Similarity	NPD6115	Approved
0.6739	Remote Similarity	NPD6697	Approved
0.6739	Remote Similarity	NPD6118	Approved
0.6729	Remote Similarity	NPD6008	Approved
0.6726	Remote Similarity	NPD6009	Approved
0.6726	Remote Similarity	NPD6317	Approved
0.6705	Remote Similarity	NPD4244	Approved
0.6705	Remote Similarity	NPD4245	Approved
0.6703	Remote Similarity	NPD6933	Approved
0.6702	Remote Similarity	NPD8028	Phase 2
0.67	Remote Similarity	NPD5281	Approved
0.67	Remote Similarity	NPD5284	Approved
0.6696	Remote Similarity	NPD6054	Approved
0.6695	Remote Similarity	NPD7507	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD6314	Approved
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD4785	Approved
0.6667	Remote Similarity	NPD4784	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6673	Approved
0.6633	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6629	Remote Similarity	NPD7152	Approved
0.6629	Remote Similarity	NPD4243	Approved
0.6629	Remote Similarity	NPD7151	Approved
0.6629	Remote Similarity	NPD7150	Approved
0.6628	Remote Similarity	NPD7331	Phase 2

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