NPASS Compound

Structure

NPC469322 OpenBabel07101718222D 33 37 0 0 1 0 0 0 0 0999 V2000 -1.4186 -3.4110 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0165 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0429 2.3038 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0737 -3.6718 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1476 -3.9727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4472 0.4027 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3416 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3729 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5297 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7693 -0.1860 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0226 -2.8899 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0701 -2.6874 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7693 -1.7614 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8432 -1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6741 -2.1663 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6865 0.9737 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.8432 -0.4868 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.3729 0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6265 -2.3687 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5297 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3501 -3.0203 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6865 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8432 -0.4868 0.0000 C 0 0 2 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 -3.3732 -1.2403 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2162 1.4605 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5525 -2.0678 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 1 0 0 0 0 4 27 1 0 0 0 0 5 27 1 0 0 0 0 7 29 1 0 0 0 0 9 10 1 0 0 0 0 9 20 1 0 0 0 0 10 23 1 0 0 0 0 11 15 1 0 0 0 0 11 19 1 0 0 0 0 12 16 1 0 0 0 0 12 22 1 0 0 0 0 13 14 1 0 0 0 0 13 24 1 0 0 0 0 14 28 1 0 0 0 0 15 29 1 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 1 1 6 0 0 0 18 19 1 0 0 0 0 19 20 2 0 0 0 0 20 29 1 0 0 0 0 21 31 1 1 0 0 0 22 26 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 23 30 1 0 0 0 0 24 26 1 0 0 0 0 24 32 2 0 0 0 0 25 21 1 6 0 0 0 25 27 1 0 0 0 0 25 33 1 0 0 0 0 27 33 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	454.34
Volume:	497.195
LogP:	5.414
LogD:	4.262
LogS:	-5.787
# Rotatable Bonds:	1
TPSA:	38.83
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	6
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.32
Synthetic Accessibility Score:	5.162
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.087
MDCK Permeability:	1.276476450584596e-05
Pgp-inhibitor:	0.952
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.883
30% Bioavailability (F30%):	0.97

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.376
Plasma Protein Binding (PPB):	97.66114044189453%
Volume Distribution (VD):	1.667
Pgp-substrate:	2.0723016262054443%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.673
CYP2C19-inhibitor:	0.152
CYP2C19-substrate:	0.971
CYP2C9-inhibitor:	0.2
CYP2C9-substrate:	0.127
CYP2D6-inhibitor:	0.048
CYP2D6-substrate:	0.457
CYP3A4-inhibitor:	0.676
CYP3A4-substrate:	0.872

ADMET: Excretion

Clearance (CL):	7.249
Half-life (T1/2):	0.035

ADMET: Toxicity

hERG Blockers:	0.025
Human Hepatotoxicity (H-HT):	0.33
Drug-inuced Liver Injury (DILI):	0.525
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.149
Maximum Recommended Daily Dose:	0.86
Skin Sensitization:	0.051
Carcinogencity:	0.05
Eye Corrosion:	0.005
Eye Irritation:	0.056
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC469322

Natural Product ID:	NPC469322
*Common Name:**	(8S,10R,14R)-17-[(2R,4S)-4-[(2R)-3,3-Dimethyloxiran-2-Yl]-4-Hydroxybutan-2-Yl]-4,4,8,10,14-Pentamethyl-1,2,5,6,7,9,11,12,15,16-Decahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:	(8S,10R,14R)-17-[(2R,4S)-4-[(2R)-3,3-dimethyloxiran-2-yl]-4-hydroxybutan-2-yl]-4,4,8,10,14-pentamethyl-1,2,5,6,7,9,11,12,15,16-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	FRARORPBMYOKKW-CHGXIUEWSA-N
Standard InCHI:	InChI=1S/C30H48O3/c1-18(17-21(31)25-27(4,5)33-25)19-11-15-29(7)20(19)9-10-23-28(6)14-13-24(32)26(2,3)22(28)12-16-30(23,29)8/h18,21-23,25,31H,9-17H2,1-8H3/t18-,21+,22?,23?,25-,28+,29+,30+/m1/s1
SMILES:	O[C@H]([C@H]1OC1(C)C)C[C@H](C1=C2CCC3[C@]([C@]2(CC1)C)(C)CCC1[C@]3(C)CCC(=O)C1(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL105206
PubChem CID:	10389368
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

*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
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	rhizome	n.a.	n.a.	PMID[10560729]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	rhizome	n.a.	PMID[17541191]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	Rhizome	n.a.	n.a.	PMID[26425784]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	tuber	n.a.	PMID[26666273]
NPO30648	Alisma orientale	Species	Alismataceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	5

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	3.9	%	PMID[509851]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	0.7	%	PMID[509851]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	38.7	%	PMID[509851]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	107.1	%	PMID[509851]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	106.5	%	PMID[509851]
NPT32	Organism	Mus musculus	Mus musculus	IC50	>	10000.0	nM	PMID[509851]

☑ 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 NPC469322 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	212
0.1-0.2	1574
0.2-0.3	6129
0.3-0.4	15653
0.4-0.5	6743
0.5-0.6	6218
0.6-0.7	5450
0.7-0.8	665
0.8-0.85	29
0.85-0.9	19
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9419	High Similarity	NPC274046
0.9419	High Similarity	NPC198074
0.9268	High Similarity	NPC86370
0.908	High Similarity	NPC473166
0.908	High Similarity	NPC262870
0.8889	High Similarity	NPC471777
0.8876	High Similarity	NPC174051
0.8876	High Similarity	NPC67831
0.8837	High Similarity	NPC469314
0.8837	High Similarity	NPC469317
0.8837	High Similarity	NPC241875
0.8778	High Similarity	NPC473415
0.8778	High Similarity	NPC180557
0.8778	High Similarity	NPC37787
0.8778	High Similarity	NPC469329
0.8778	High Similarity	NPC30677
0.8667	High Similarity	NPC318332
0.8636	High Similarity	NPC469323
0.8617	High Similarity	NPC469316
0.8511	High Similarity	NPC469327
0.8511	High Similarity	NPC476897
0.8495	Intermediate Similarity	NPC303777
0.8495	Intermediate Similarity	NPC471784
0.8488	Intermediate Similarity	NPC473157
0.8409	Intermediate Similarity	NPC90652
0.8351	Intermediate Similarity	NPC470587
0.8315	Intermediate Similarity	NPC470417
0.828	Intermediate Similarity	NPC471822
0.8265	Intermediate Similarity	NPC473165
0.8265	Intermediate Similarity	NPC471783
0.8265	Intermediate Similarity	NPC9457
0.8261	Intermediate Similarity	NPC240617
0.8242	Intermediate Similarity	NPC473167
0.8222	Intermediate Similarity	NPC469319
0.8222	Intermediate Similarity	NPC229871
0.8144	Intermediate Similarity	NPC324001
0.8125	Intermediate Similarity	NPC473174
0.8111	Intermediate Similarity	NPC44181
0.8095	Intermediate Similarity	NPC149249
0.809	Intermediate Similarity	NPC471737
0.809	Intermediate Similarity	NPC89077
0.809	Intermediate Similarity	NPC473168
0.8065	Intermediate Similarity	NPC473172
0.8041	Intermediate Similarity	NPC473163
0.8022	Intermediate Similarity	NPC32830
0.8021	Intermediate Similarity	NPC473176
0.8021	Intermediate Similarity	NPC167974
0.8	Intermediate Similarity	NPC99909
0.8	Intermediate Similarity	NPC251808
0.8	Intermediate Similarity	NPC474174
0.8	Intermediate Similarity	NPC138756
0.7979	Intermediate Similarity	NPC473170
0.7959	Intermediate Similarity	NPC239716
0.7957	Intermediate Similarity	NPC469315
0.7955	Intermediate Similarity	NPC472744
0.7912	Intermediate Similarity	NPC193360
0.7912	Intermediate Similarity	NPC255176
0.7907	Intermediate Similarity	NPC476812
0.7907	Intermediate Similarity	NPC215843
0.79	Intermediate Similarity	NPC469318
0.79	Intermediate Similarity	NPC473173
0.7895	Intermediate Similarity	NPC473164
0.7889	Intermediate Similarity	NPC324063
0.7889	Intermediate Similarity	NPC125399
0.7882	Intermediate Similarity	NPC264602
0.7882	Intermediate Similarity	NPC325946
0.7865	Intermediate Similarity	NPC85774
0.7865	Intermediate Similarity	NPC59453
0.7865	Intermediate Similarity	NPC82902
0.7865	Intermediate Similarity	NPC221758
0.7865	Intermediate Similarity	NPC214043
0.7857	Intermediate Similarity	NPC473928
0.7841	Intermediate Similarity	NPC151519
0.7841	Intermediate Similarity	NPC469325
0.7841	Intermediate Similarity	NPC477858
0.7841	Intermediate Similarity	NPC212083
0.7841	Intermediate Similarity	NPC145143
0.7826	Intermediate Similarity	NPC215029
0.7826	Intermediate Similarity	NPC250592
0.7826	Intermediate Similarity	NPC122116
0.7826	Intermediate Similarity	NPC77263
0.7826	Intermediate Similarity	NPC476733
0.7812	Intermediate Similarity	NPC272451
0.78	Intermediate Similarity	NPC472655
0.7778	Intermediate Similarity	NPC471224
0.7778	Intermediate Similarity	NPC474218
0.7778	Intermediate Similarity	NPC471005
0.7766	Intermediate Similarity	NPC141447
0.7753	Intermediate Similarity	NPC259173
0.7742	Intermediate Similarity	NPC126993
0.7742	Intermediate Similarity	NPC171441
0.7742	Intermediate Similarity	NPC289213
0.7742	Intermediate Similarity	NPC472307
0.7742	Intermediate Similarity	NPC85173
0.7742	Intermediate Similarity	NPC136801
0.7738	Intermediate Similarity	NPC470299
0.7732	Intermediate Similarity	NPC471582
0.7727	Intermediate Similarity	NPC77311
0.7727	Intermediate Similarity	NPC3915
0.7717	Intermediate Similarity	NPC474677
0.7708	Intermediate Similarity	NPC91439
0.7701	Intermediate Similarity	NPC201459
0.7701	Intermediate Similarity	NPC245029
0.7701	Intermediate Similarity	NPC31302
0.77	Intermediate Similarity	NPC75531
0.77	Intermediate Similarity	NPC473175
0.77	Intermediate Similarity	NPC149124
0.77	Intermediate Similarity	NPC100955
0.77	Intermediate Similarity	NPC121566
0.7692	Intermediate Similarity	NPC472745
0.7692	Intermediate Similarity	NPC213412
0.7692	Intermediate Similarity	NPC474733
0.7692	Intermediate Similarity	NPC51014
0.7692	Intermediate Similarity	NPC469994
0.7692	Intermediate Similarity	NPC474732
0.7692	Intermediate Similarity	NPC145879
0.7692	Intermediate Similarity	NPC31564
0.7692	Intermediate Similarity	NPC474448
0.7692	Intermediate Similarity	NPC474778
0.767	Intermediate Similarity	NPC470065
0.7667	Intermediate Similarity	NPC329043
0.7667	Intermediate Similarity	NPC321187
0.7667	Intermediate Similarity	NPC58841
0.7667	Intermediate Similarity	NPC473246
0.7667	Intermediate Similarity	NPC161423
0.7667	Intermediate Similarity	NPC227064
0.7667	Intermediate Similarity	NPC180834
0.766	Intermediate Similarity	NPC155304
0.764	Intermediate Similarity	NPC310989
0.7634	Intermediate Similarity	NPC76879
0.7634	Intermediate Similarity	NPC31985
0.7634	Intermediate Similarity	NPC2983
0.7634	Intermediate Similarity	NPC1015
0.7634	Intermediate Similarity	NPC474245
0.7629	Intermediate Similarity	NPC473161
0.7624	Intermediate Similarity	NPC63023
0.7624	Intermediate Similarity	NPC95243
0.7614	Intermediate Similarity	NPC2482
0.7609	Intermediate Similarity	NPC93778
0.7609	Intermediate Similarity	NPC317590
0.7609	Intermediate Similarity	NPC475740
0.7609	Intermediate Similarity	NPC202937
0.7609	Intermediate Similarity	NPC58063
0.7604	Intermediate Similarity	NPC279974
0.76	Intermediate Similarity	NPC264048
0.7582	Intermediate Similarity	NPC470574
0.7582	Intermediate Similarity	NPC197823
0.7582	Intermediate Similarity	NPC274724
0.7582	Intermediate Similarity	NPC469948
0.7582	Intermediate Similarity	NPC133954
0.7582	Intermediate Similarity	NPC474083
0.7582	Intermediate Similarity	NPC76518
0.7579	Intermediate Similarity	NPC12722
0.7579	Intermediate Similarity	NPC107674
0.7579	Intermediate Similarity	NPC170220
0.7579	Intermediate Similarity	NPC141497
0.7579	Intermediate Similarity	NPC474736
0.7573	Intermediate Similarity	NPC41405
0.7556	Intermediate Similarity	NPC217559
0.7556	Intermediate Similarity	NPC292458
0.7556	Intermediate Similarity	NPC472743
0.7556	Intermediate Similarity	NPC475726
0.7556	Intermediate Similarity	NPC132635
0.7556	Intermediate Similarity	NPC268578
0.7556	Intermediate Similarity	NPC215893
0.7553	Intermediate Similarity	NPC219495
0.7553	Intermediate Similarity	NPC320026
0.7551	Intermediate Similarity	NPC119036
0.7549	Intermediate Similarity	NPC255387
0.7549	Intermediate Similarity	NPC144459
0.7549	Intermediate Similarity	NPC131665
0.7547	Intermediate Similarity	NPC284915
0.7529	Intermediate Similarity	NPC472854
0.7528	Intermediate Similarity	NPC474484
0.7528	Intermediate Similarity	NPC103754
0.7527	Intermediate Similarity	NPC254572
0.7527	Intermediate Similarity	NPC328313
0.7527	Intermediate Similarity	NPC229407
0.7527	Intermediate Similarity	NPC310752
0.7527	Intermediate Similarity	NPC292491
0.7527	Intermediate Similarity	NPC48824
0.7527	Intermediate Similarity	NPC53911
0.7527	Intermediate Similarity	NPC250687
0.7526	Intermediate Similarity	NPC327788
0.7526	Intermediate Similarity	NPC230151
0.7526	Intermediate Similarity	NPC471039
0.7526	Intermediate Similarity	NPC160056
0.7525	Intermediate Similarity	NPC471293
0.75	Intermediate Similarity	NPC158393
0.75	Intermediate Similarity	NPC325594
0.75	Intermediate Similarity	NPC92139
0.75	Intermediate Similarity	NPC73038
0.75	Intermediate Similarity	NPC72133
0.75	Intermediate Similarity	NPC74363
0.75	Intermediate Similarity	NPC179591
0.75	Intermediate Similarity	NPC209662
0.75	Intermediate Similarity	NPC20688
0.75	Intermediate Similarity	NPC56588
0.75	Intermediate Similarity	NPC159410
0.75	Intermediate Similarity	NPC70661

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 NPC469322 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	185
0.1-0.2	1984
0.2-0.3	4110
0.3-0.4	1976
0.4-0.5	485
0.5-0.6	189
0.6-0.7	204
0.7-0.8	17
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
0.7865	Intermediate Similarity	NPD4786	Approved
0.7841	Intermediate Similarity	NPD3667	Approved
0.7667	Intermediate Similarity	NPD3665	Phase 1
0.7667	Intermediate Similarity	NPD3133	Approved
0.7667	Intermediate Similarity	NPD3666	Approved
0.7556	Intermediate Similarity	NPD4788	Approved
0.75	Intermediate Similarity	NPD3618	Phase 1
0.7449	Intermediate Similarity	NPD6084	Phase 2
0.7449	Intermediate Similarity	NPD6083	Phase 2
0.7447	Intermediate Similarity	NPD5328	Approved
0.7447	Intermediate Similarity	NPD4753	Phase 2
0.7396	Intermediate Similarity	NPD6399	Phase 3
0.7386	Intermediate Similarity	NPD3617	Approved
0.7381	Intermediate Similarity	NPD4244	Approved
0.7381	Intermediate Similarity	NPD4245	Approved
0.7379	Intermediate Similarity	NPD6412	Phase 2
0.734	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7312	Intermediate Similarity	NPD6684	Approved
0.7312	Intermediate Similarity	NPD5330	Approved
0.7312	Intermediate Similarity	NPD7521	Approved
0.7312	Intermediate Similarity	NPD7334	Approved
0.7312	Intermediate Similarity	NPD6409	Approved
0.7312	Intermediate Similarity	NPD7146	Approved
0.7294	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD6079	Approved
0.7262	Intermediate Similarity	NPD3698	Phase 2
0.7262	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7253	Intermediate Similarity	NPD4223	Phase 3
0.7253	Intermediate Similarity	NPD4221	Approved
0.7248	Intermediate Similarity	NPD7115	Discovery
0.7238	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD4202	Approved
0.7204	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5329	Approved
0.7176	Intermediate Similarity	NPD4789	Approved
0.7158	Intermediate Similarity	NPD6903	Approved
0.7143	Intermediate Similarity	NPD4692	Approved
0.7143	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD4139	Approved
0.7128	Intermediate Similarity	NPD5279	Phase 3
0.7115	Intermediate Similarity	NPD5739	Approved
0.7115	Intermediate Similarity	NPD6675	Approved
0.7115	Intermediate Similarity	NPD6402	Approved
0.7115	Intermediate Similarity	NPD7128	Approved
0.7113	Intermediate Similarity	NPD7515	Phase 2
0.71	Intermediate Similarity	NPD4755	Approved
0.7097	Intermediate Similarity	NPD3668	Phase 3
0.7097	Intermediate Similarity	NPD4197	Approved
0.7071	Intermediate Similarity	NPD4629	Approved
0.7071	Intermediate Similarity	NPD5695	Phase 3
0.7071	Intermediate Similarity	NPD5210	Approved
0.7037	Intermediate Similarity	NPD8297	Approved
0.7033	Intermediate Similarity	NPD7525	Registered
0.703	Intermediate Similarity	NPD5696	Approved
0.6988	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6981	Remote Similarity	NPD6899	Approved
0.6981	Remote Similarity	NPD7320	Approved
0.6981	Remote Similarity	NPD6881	Approved
0.6979	Remote Similarity	NPD6672	Approved
0.6979	Remote Similarity	NPD5737	Approved
0.6966	Remote Similarity	NPD6933	Approved
0.6961	Remote Similarity	NPD5286	Approved
0.6961	Remote Similarity	NPD5285	Approved
0.6961	Remote Similarity	NPD4700	Approved
0.6961	Remote Similarity	NPD4696	Approved
0.6947	Remote Similarity	NPD4623	Approved
0.6947	Remote Similarity	NPD4693	Phase 3
0.6947	Remote Similarity	NPD4519	Discontinued
0.6947	Remote Similarity	NPD4689	Approved
0.6947	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD4138	Approved
0.6947	Remote Similarity	NPD5205	Approved
0.6947	Remote Similarity	NPD4688	Approved
0.6947	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6098	Approved
0.6941	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6941	Remote Similarity	NPD5360	Phase 3
0.6939	Remote Similarity	NPD8035	Phase 2
0.6939	Remote Similarity	NPD8034	Phase 2
0.6932	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7902	Approved
0.6923	Remote Similarity	NPD7645	Phase 2
0.6916	Remote Similarity	NPD6372	Approved
0.6916	Remote Similarity	NPD6373	Approved
0.6916	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5777	Approved
0.6887	Remote Similarity	NPD5701	Approved
0.6887	Remote Similarity	NPD5697	Approved
0.6875	Remote Similarity	NPD7524	Approved
0.6863	Remote Similarity	NPD7638	Approved
0.6854	Remote Similarity	NPD3703	Phase 2
0.6854	Remote Similarity	NPD7339	Approved
0.6854	Remote Similarity	NPD6942	Approved
0.6852	Remote Similarity	NPD6883	Approved
0.6852	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD7290	Approved
0.6852	Remote Similarity	NPD7102	Approved
0.6832	Remote Similarity	NPD5222	Approved
0.6832	Remote Similarity	NPD4697	Phase 3
0.6832	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD5221	Approved
0.6827	Remote Similarity	NPD5211	Phase 2
0.6827	Remote Similarity	NPD5225	Approved
0.6827	Remote Similarity	NPD5224	Approved
0.6827	Remote Similarity	NPD4633	Approved
0.6827	Remote Similarity	NPD5226	Approved
0.6822	Remote Similarity	NPD6686	Approved
0.6796	Remote Similarity	NPD7640	Approved
0.6796	Remote Similarity	NPD7639	Approved
0.6789	Remote Similarity	NPD8130	Phase 1
0.6789	Remote Similarity	NPD6847	Approved
0.6789	Remote Similarity	NPD6650	Approved
0.6789	Remote Similarity	NPD6869	Approved
0.6789	Remote Similarity	NPD6649	Approved
0.6789	Remote Similarity	NPD6617	Approved
0.6778	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD6117	Approved
0.6771	Remote Similarity	NPD5690	Phase 2
0.6771	Remote Similarity	NPD5280	Approved
0.6771	Remote Similarity	NPD4694	Approved
0.6765	Remote Similarity	NPD5173	Approved
0.6762	Remote Similarity	NPD5174	Approved
0.6762	Remote Similarity	NPD5175	Approved
0.6759	Remote Similarity	NPD6014	Approved
0.6759	Remote Similarity	NPD6012	Approved
0.6759	Remote Similarity	NPD6013	Approved
0.6742	Remote Similarity	NPD6926	Approved
0.6742	Remote Similarity	NPD6924	Approved
0.6735	Remote Similarity	NPD6904	Approved
0.6735	Remote Similarity	NPD6673	Approved
0.6735	Remote Similarity	NPD6080	Approved
0.6733	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD4159	Approved
0.6731	Remote Similarity	NPD5223	Approved
0.6727	Remote Similarity	NPD6882	Approved
0.6703	Remote Similarity	NPD6116	Phase 1
0.6698	Remote Similarity	NPD5141	Approved
0.6697	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3702	Approved
0.6667	Remote Similarity	NPD4695	Discontinued
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6011	Approved
0.6667	Remote Similarity	NPD4632	Approved
0.6636	Remote Similarity	NPD4768	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD4767	Approved
0.6634	Remote Similarity	NPD7900	Approved
0.6634	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD5208	Approved
0.6632	Remote Similarity	NPD6695	Phase 3
0.663	Remote Similarity	NPD6114	Approved
0.663	Remote Similarity	NPD6115	Approved
0.663	Remote Similarity	NPD3671	Phase 1
0.663	Remote Similarity	NPD6697	Approved
0.663	Remote Similarity	NPD6118	Approved
0.6609	Remote Similarity	NPD6059	Approved
0.6609	Remote Similarity	NPD6319	Approved
0.6609	Remote Similarity	NPD6054	Approved
0.6604	Remote Similarity	NPD4754	Approved
0.66	Remote Similarity	NPD6411	Approved
0.6574	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6566	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6559	Remote Similarity	NPD4195	Approved
0.6538	Remote Similarity	NPD4225	Approved
0.6535	Remote Similarity	NPD5133	Approved
0.6518	Remote Similarity	NPD8133	Approved
0.6517	Remote Similarity	NPD4243	Approved
0.6517	Remote Similarity	NPD6081	Approved
0.6517	Remote Similarity	NPD4758	Discontinued
0.6514	Remote Similarity	NPD4729	Approved
0.6514	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD4730	Approved
0.6514	Remote Similarity	NPD5128	Approved
0.6512	Remote Similarity	NPD4224	Phase 2
0.6496	Remote Similarity	NPD6370	Approved
0.6491	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6931	Approved
0.6489	Remote Similarity	NPD6930	Phase 2
0.6489	Remote Similarity	NPD4748	Discontinued
0.6489	Remote Similarity	NPD7509	Discontinued
0.6481	Remote Similarity	NPD6008	Approved
0.6477	Remote Similarity	NPD4137	Phase 3
0.6471	Remote Similarity	NPD7507	Approved
0.6471	Remote Similarity	NPD6001	Approved
0.6441	Remote Similarity	NPD7604	Phase 2
0.6436	Remote Similarity	NPD5281	Approved
0.6436	Remote Similarity	NPD5284	Approved
0.6436	Remote Similarity	NPD6050	Approved
0.6436	Remote Similarity	NPD5693	Phase 1
0.641	Remote Similarity	NPD6015	Approved
0.641	Remote Similarity	NPD6016	Approved
0.6404	Remote Similarity	NPD4691	Approved
0.6404	Remote Similarity	NPD4747	Approved
0.6404	Remote Similarity	NPD6274	Approved
0.64	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6101	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