NPASS Compound

Structure

NPC469325 OpenBabel07101718222D 34 37 0 0 1 0 0 0 0 0999 V2000 0.5754 -2.9242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8532 -5.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0556 -4.6778 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8861 2.7906 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8598 2.7906 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 0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3960 0.8895 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 -1.6865 -0.9737 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6865 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2162 0.4868 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 -0.8432 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1793 -2.4030 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8287 -4.0527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9260 0.3009 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2269 -2.2006 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.4802 -3.3291 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 1.4983 -0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 1.4605 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.6865 -0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.2162 1.4605 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9260 -1.2746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1296 -4.9787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3729 1.9474 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5297 0.4868 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 3.4326 -3.5315 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.4720 -0.4868 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0594 1.9474 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4780 -5.7023 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 14 1 0 0 0 0 11 22 1 0 0 0 0 12 13 1 0 0 0 0 12 24 1 0 0 0 0 13 28 1 0 0 0 0 14 29 1 0 0 0 0 15 18 1 0 0 0 0 15 19 1 0 0 0 0 16 19 1 0 0 0 0 16 26 1 0 0 0 0 17 21 1 0 0 0 0 17 30 1 0 0 0 0 18 1 1 1 0 0 0 18 25 1 0 0 0 0 19 31 2 0 0 0 0 20 25 2 0 0 0 0 20 30 1 0 0 0 0 21 25 1 0 0 0 0 21 32 2 0 0 0 0 22 27 1 0 0 0 0 22 28 1 0 0 0 0 23 28 1 0 0 0 0 23 29 1 0 0 0 0 24 27 1 0 0 0 0 24 33 2 0 0 0 0 26 34 1 0 0 0 0 28 6 1 6 0 0 0 29 30 1 6 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	238.19
Volume:	265.827
LogP:	3.165
LogD:	2.689
LogS:	-3.524
# Rotatable Bonds:	1
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	2
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.69
Synthetic Accessibility Score:	4.352
Fsp3:	0.867
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.223
MDCK Permeability:	1.938422428793274e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.436
30% Bioavailability (F30%):	0.063

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.518
Plasma Protein Binding (PPB):	89.00637817382812%
Volume Distribution (VD):	1.132
Pgp-substrate:	11.168731689453125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.12
CYP1A2-substrate:	0.424
CYP2C19-inhibitor:	0.083
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.106
CYP2C9-substrate:	0.364
CYP2D6-inhibitor:	0.025
CYP2D6-substrate:	0.216
CYP3A4-inhibitor:	0.2
CYP3A4-substrate:	0.556

ADMET: Excretion

Clearance (CL):	8.893
Half-life (T1/2):	0.261

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.135
Drug-inuced Liver Injury (DILI):	0.31
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.127
Maximum Recommended Daily Dose:	0.175
Skin Sensitization:	0.038
Carcinogencity:	0.523
Eye Corrosion:	0.004
Eye Irritation:	0.066
Respiratory Toxicity:	0.174

Download Data

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

Natural Product: NPC469325

Natural Product ID:	NPC469325
*Common Name:**	(8S,10R,14R)-17-[(2R)-6-Hydroxy-6-Methyl-4-Oxoheptan-2-Yl]-4,4,8,10,14-Pentamethyl-2,5,6,7,9,11,12,15-Octahydro-1H-Cyclopenta[A]Phenanthrene-3,16-Dione
IUPAC Name:	(8S,10R,14R)-17-[(2R)-6-hydroxy-6-methyl-4-oxoheptan-2-yl]-4,4,8,10,14-pentamethyl-2,5,6,7,9,11,12,15-octahydro-1H-cyclopenta[a]phenanthrene-3,16-dione
Synonyms:
Standard InCHIKey:	JYXPQVJIQKXCLQ-OICVSACGSA-N
Standard InCHI:	InChI=1S/C30H46O4/c1-18(15-19(31)16-26(2,3)34)25-20-9-10-23-28(6)13-12-24(33)27(4,5)22(28)11-14-29(23,7)30(20,8)17-21(25)32/h18,22-23,34H,9-17H2,1-8H3/t18-,22?,23?,28+,29+,30+/m1/s1
SMILES:	CC(CC(=O)CC(C)(C)O)C1=C2CCC3C4(CCC(=O)C(C4CCC3(C2(CC1=O)C)C)(C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL105499
PubChem CID:	44335331
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	=	-5.1	%	PMID[561967]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	17.2	%	PMID[561967]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	26.7	%	PMID[561967]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	71.3	%	PMID[561967]
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	97.2	%	PMID[561967]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	17000.0	nM	PMID[561967]

☑ 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 NPC469325 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	197
0.1-0.2	1670
0.2-0.3	7819
0.3-0.4	14750
0.4-0.5	8271
0.5-0.6	5990
0.6-0.7	3349
0.7-0.8	635
0.8-0.85	15
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8434	Intermediate Similarity	NPC86370
0.8395	Intermediate Similarity	NPC215843
0.8256	Intermediate Similarity	NPC99909
0.8242	Intermediate Similarity	NPC473161
0.8235	Intermediate Similarity	NPC473038
0.8193	Intermediate Similarity	NPC189237
0.8193	Intermediate Similarity	NPC473217
0.814	Intermediate Similarity	NPC471737
0.8118	Intermediate Similarity	NPC209882
0.8095	Intermediate Similarity	NPC193347
0.8072	Intermediate Similarity	NPC18955
0.8049	Intermediate Similarity	NPC476808
0.8046	Intermediate Similarity	NPC469314
0.8046	Intermediate Similarity	NPC241875
0.8046	Intermediate Similarity	NPC469317
0.8046	Intermediate Similarity	NPC136948
0.8023	Intermediate Similarity	NPC123319
0.8023	Intermediate Similarity	NPC94531
0.8023	Intermediate Similarity	NPC311702
0.8	Intermediate Similarity	NPC474807
0.8	Intermediate Similarity	NPC477373
0.7976	Intermediate Similarity	NPC44963
0.7976	Intermediate Similarity	NPC472684
0.7976	Intermediate Similarity	NPC471898
0.7976	Intermediate Similarity	NPC278459
0.7952	Intermediate Similarity	NPC192329
0.7935	Intermediate Similarity	NPC473164
0.7931	Intermediate Similarity	NPC475181
0.7931	Intermediate Similarity	NPC229717
0.7931	Intermediate Similarity	NPC158393
0.7931	Intermediate Similarity	NPC472869
0.7907	Intermediate Similarity	NPC144258
0.7907	Intermediate Similarity	NPC214043
0.7907	Intermediate Similarity	NPC472480
0.7907	Intermediate Similarity	NPC248758
0.7907	Intermediate Similarity	NPC96095
0.7907	Intermediate Similarity	NPC85774
0.7882	Intermediate Similarity	NPC320514
0.7865	Intermediate Similarity	NPC262043
0.7865	Intermediate Similarity	NPC184663
0.7857	Intermediate Similarity	NPC476809
0.7857	Intermediate Similarity	NPC2482
0.7857	Intermediate Similarity	NPC279667
0.7857	Intermediate Similarity	NPC37038
0.7841	Intermediate Similarity	NPC469322
0.7841	Intermediate Similarity	NPC96496
0.7841	Intermediate Similarity	NPC476409
0.7841	Intermediate Similarity	NPC93778
0.7831	Intermediate Similarity	NPC275494
0.7831	Intermediate Similarity	NPC471409
0.7831	Intermediate Similarity	NPC30321
0.7816	Intermediate Similarity	NPC29447
0.7816	Intermediate Similarity	NPC469948
0.7816	Intermediate Similarity	NPC197823
0.7805	Intermediate Similarity	NPC92080
0.7802	Intermediate Similarity	NPC233118
0.7791	Intermediate Similarity	NPC271784
0.7791	Intermediate Similarity	NPC167103
0.7791	Intermediate Similarity	NPC472492
0.7791	Intermediate Similarity	NPC53733
0.7791	Intermediate Similarity	NPC168188
0.7791	Intermediate Similarity	NPC470015
0.7778	Intermediate Similarity	NPC252737
0.7778	Intermediate Similarity	NPC85173
0.7778	Intermediate Similarity	NPC126993
0.7765	Intermediate Similarity	NPC116797
0.7765	Intermediate Similarity	NPC147066
0.7765	Intermediate Similarity	NPC477372
0.7753	Intermediate Similarity	NPC472870
0.7753	Intermediate Similarity	NPC474677
0.775	Intermediate Similarity	NPC144627
0.775	Intermediate Similarity	NPC223187
0.7742	Intermediate Similarity	NPC29152
0.7738	Intermediate Similarity	NPC231431
0.7727	Intermediate Similarity	NPC31564
0.7727	Intermediate Similarity	NPC474778
0.7727	Intermediate Similarity	NPC474733
0.7727	Intermediate Similarity	NPC474732
0.7727	Intermediate Similarity	NPC472479
0.7727	Intermediate Similarity	NPC145879
0.7717	Intermediate Similarity	NPC473172
0.7717	Intermediate Similarity	NPC318332
0.7711	Intermediate Similarity	NPC165711
0.7711	Intermediate Similarity	NPC66105
0.7701	Intermediate Similarity	NPC473246
0.7701	Intermediate Similarity	NPC329043
0.7701	Intermediate Similarity	NPC473157
0.7701	Intermediate Similarity	NPC19849
0.7701	Intermediate Similarity	NPC237712
0.7701	Intermediate Similarity	NPC58841
0.7701	Intermediate Similarity	NPC161423
0.7701	Intermediate Similarity	NPC227064
0.7701	Intermediate Similarity	NPC472864
0.7701	Intermediate Similarity	NPC321187
0.7692	Intermediate Similarity	NPC473166
0.7692	Intermediate Similarity	NPC230064
0.7683	Intermediate Similarity	NPC201027
0.7674	Intermediate Similarity	NPC477270
0.7674	Intermediate Similarity	NPC302661
0.7674	Intermediate Similarity	NPC238991
0.7674	Intermediate Similarity	NPC477269
0.7674	Intermediate Similarity	NPC129080
0.7674	Intermediate Similarity	NPC477271
0.7667	Intermediate Similarity	NPC68148
0.7667	Intermediate Similarity	NPC65615
0.7667	Intermediate Similarity	NPC477943
0.7667	Intermediate Similarity	NPC469319
0.7667	Intermediate Similarity	NPC229871
0.7667	Intermediate Similarity	NPC326627
0.7667	Intermediate Similarity	NPC310010
0.7667	Intermediate Similarity	NPC474570
0.7667	Intermediate Similarity	NPC31985
0.7667	Intermediate Similarity	NPC1015
0.766	Intermediate Similarity	NPC477268
0.766	Intermediate Similarity	NPC472689
0.766	Intermediate Similarity	NPC472690
0.766	Intermediate Similarity	NPC477267
0.766	Intermediate Similarity	NPC156546
0.7647	Intermediate Similarity	NPC824
0.7647	Intermediate Similarity	NPC26139
0.7647	Intermediate Similarity	NPC469637
0.7647	Intermediate Similarity	NPC287817
0.7647	Intermediate Similarity	NPC138492
0.7647	Intermediate Similarity	NPC74445
0.7647	Intermediate Similarity	NPC233352
0.764	Intermediate Similarity	NPC475740
0.764	Intermediate Similarity	NPC472481
0.764	Intermediate Similarity	NPC158141
0.764	Intermediate Similarity	NPC58063
0.764	Intermediate Similarity	NPC472482
0.764	Intermediate Similarity	NPC472484
0.764	Intermediate Similarity	NPC90652
0.764	Intermediate Similarity	NPC173089
0.7634	Intermediate Similarity	NPC280725
0.7634	Intermediate Similarity	NPC473170
0.7619	Intermediate Similarity	NPC280654
0.7619	Intermediate Similarity	NPC260385
0.7619	Intermediate Similarity	NPC110094
0.7614	Intermediate Similarity	NPC470574
0.7614	Intermediate Similarity	NPC142649
0.7614	Intermediate Similarity	NPC469993
0.7614	Intermediate Similarity	NPC201655
0.7614	Intermediate Similarity	NPC474537
0.7614	Intermediate Similarity	NPC11711
0.7609	Intermediate Similarity	NPC131840
0.7609	Intermediate Similarity	NPC274046
0.7609	Intermediate Similarity	NPC198074
0.759	Intermediate Similarity	NPC246445
0.759	Intermediate Similarity	NPC89294
0.759	Intermediate Similarity	NPC239758
0.759	Intermediate Similarity	NPC180886
0.7586	Intermediate Similarity	NPC476100
0.7586	Intermediate Similarity	NPC105803
0.7586	Intermediate Similarity	NPC469561
0.7586	Intermediate Similarity	NPC102197
0.7582	Intermediate Similarity	NPC476437
0.7582	Intermediate Similarity	NPC472866
0.7582	Intermediate Similarity	NPC476369
0.7579	Intermediate Similarity	NPC147954
0.7564	Intermediate Similarity	NPC103734
0.7561	Intermediate Similarity	NPC470299
0.7561	Intermediate Similarity	NPC162164
0.7558	Intermediate Similarity	NPC267691
0.7558	Intermediate Similarity	NPC3915
0.7558	Intermediate Similarity	NPC142244
0.7558	Intermediate Similarity	NPC38350
0.7558	Intermediate Similarity	NPC162632
0.7558	Intermediate Similarity	NPC121984
0.7558	Intermediate Similarity	NPC263272
0.7558	Intermediate Similarity	NPC201912
0.7558	Intermediate Similarity	NPC221647
0.7558	Intermediate Similarity	NPC274050
0.7558	Intermediate Similarity	NPC150506
0.7558	Intermediate Similarity	NPC55869
0.7556	Intermediate Similarity	NPC474511
0.7556	Intermediate Similarity	NPC117122
0.7556	Intermediate Similarity	NPC72397
0.7556	Intermediate Similarity	NPC476796
0.7556	Intermediate Similarity	NPC53911
0.7556	Intermediate Similarity	NPC470417
0.7556	Intermediate Similarity	NPC328313
0.7556	Intermediate Similarity	NPC230387
0.7556	Intermediate Similarity	NPC193360
0.7556	Intermediate Similarity	NPC1753
0.7556	Intermediate Similarity	NPC471724
0.7556	Intermediate Similarity	NPC472483
0.7529	Intermediate Similarity	NPC476812
0.7529	Intermediate Similarity	NPC192744
0.7529	Intermediate Similarity	NPC301769
0.7529	Intermediate Similarity	NPC477371
0.7529	Intermediate Similarity	NPC32758
0.7529	Intermediate Similarity	NPC201459
0.7529	Intermediate Similarity	NPC199595
0.7528	Intermediate Similarity	NPC194417
0.7528	Intermediate Similarity	NPC327115
0.7528	Intermediate Similarity	NPC72133
0.7528	Intermediate Similarity	NPC472488
0.7528	Intermediate Similarity	NPC472494
0.7528	Intermediate Similarity	NPC472491
0.7527	Intermediate Similarity	NPC124207

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 NPC469325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	2107
0.2-0.3	4210
0.3-0.4	1854
0.4-0.5	428
0.5-0.6	153
0.6-0.7	173
0.7-0.8	39
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
0.8353	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.8272	Intermediate Similarity	NPD3617	Approved
0.8095	Intermediate Similarity	NPD4221	Approved
0.8095	Intermediate Similarity	NPD4223	Phase 3
0.8023	Intermediate Similarity	NPD5329	Approved
0.7907	Intermediate Similarity	NPD4197	Approved
0.7727	Intermediate Similarity	NPD5205	Approved
0.7727	Intermediate Similarity	NPD4689	Approved
0.7727	Intermediate Similarity	NPD4693	Phase 3
0.7727	Intermediate Similarity	NPD4519	Discontinued
0.7727	Intermediate Similarity	NPD4138	Approved
0.7727	Intermediate Similarity	NPD4690	Approved
0.7727	Intermediate Similarity	NPD4688	Approved
0.7727	Intermediate Similarity	NPD4623	Approved
0.7701	Intermediate Similarity	NPD3666	Approved
0.7701	Intermediate Similarity	NPD3665	Phase 1
0.7701	Intermediate Similarity	NPD3133	Approved
0.7667	Intermediate Similarity	NPD4753	Phase 2
0.7647	Intermediate Similarity	NPD4695	Discontinued
0.7634	Intermediate Similarity	NPD4629	Approved
0.7634	Intermediate Similarity	NPD5210	Approved
0.7586	Intermediate Similarity	NPD4788	Approved
0.7558	Intermediate Similarity	NPD4692	Approved
0.7558	Intermediate Similarity	NPD4139	Approved
0.7531	Intermediate Similarity	NPD6081	Approved
0.7528	Intermediate Similarity	NPD4694	Approved
0.7528	Intermediate Similarity	NPD3618	Phase 1
0.7528	Intermediate Similarity	NPD5690	Phase 2
0.7528	Intermediate Similarity	NPD5280	Approved
0.75	Intermediate Similarity	NPD4786	Approved
0.7473	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD5328	Approved
0.7471	Intermediate Similarity	NPD3667	Approved
0.7396	Intermediate Similarity	NPD5696	Approved
0.7375	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD5360	Phase 3
0.7368	Intermediate Similarity	NPD7614	Phase 1
0.7326	Intermediate Similarity	NPD4195	Approved
0.7312	Intermediate Similarity	NPD7515	Phase 2
0.7312	Intermediate Similarity	NPD5284	Approved
0.7312	Intermediate Similarity	NPD5281	Approved
0.7312	Intermediate Similarity	NPD6079	Approved
0.7292	Intermediate Similarity	NPD6083	Phase 2
0.7292	Intermediate Similarity	NPD6084	Phase 2
0.7284	Intermediate Similarity	NPD4137	Phase 3
0.7283	Intermediate Similarity	NPD6080	Approved
0.7283	Intermediate Similarity	NPD6673	Approved
0.7283	Intermediate Similarity	NPD6904	Approved
0.7234	Intermediate Similarity	NPD4202	Approved
0.7215	Intermediate Similarity	NPD7341	Phase 2
0.7195	Intermediate Similarity	NPD4747	Approved
0.7195	Intermediate Similarity	NPD4691	Approved
0.7174	Intermediate Similarity	NPD6672	Approved
0.7174	Intermediate Similarity	NPD5737	Approved
0.7174	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7172	Intermediate Similarity	NPD5091	Approved
0.7158	Intermediate Similarity	NPD7748	Approved
0.7143	Intermediate Similarity	NPD7334	Approved
0.7143	Intermediate Similarity	NPD5279	Phase 3
0.7143	Intermediate Similarity	NPD6409	Approved
0.7143	Intermediate Similarity	NPD7521	Approved
0.7143	Intermediate Similarity	NPD7146	Approved
0.7143	Intermediate Similarity	NPD6684	Approved
0.7143	Intermediate Similarity	NPD5330	Approved
0.7113	Intermediate Similarity	NPD4755	Approved
0.7111	Intermediate Similarity	NPD3668	Phase 3
0.7083	Intermediate Similarity	NPD5695	Phase 3
0.7053	Intermediate Similarity	NPD5133	Approved
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.7021	Intermediate Similarity	NPD4096	Approved
0.701	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5221	Approved
0.701	Intermediate Similarity	NPD4697	Phase 3
0.701	Intermediate Similarity	NPD5222	Approved
0.6989	Remote Similarity	NPD5208	Approved
0.6989	Remote Similarity	NPD6903	Approved
0.6988	Remote Similarity	NPD4789	Approved
0.6988	Remote Similarity	NPD4245	Approved
0.6988	Remote Similarity	NPD4244	Approved
0.697	Remote Similarity	NPD4700	Approved
0.697	Remote Similarity	NPD5286	Approved
0.697	Remote Similarity	NPD4696	Approved
0.697	Remote Similarity	NPD5285	Approved
0.6957	Remote Similarity	NPD6098	Approved
0.6947	Remote Similarity	NPD6050	Approved
0.6947	Remote Similarity	NPD5693	Phase 1
0.6941	Remote Similarity	NPD4058	Approved
0.6941	Remote Similarity	NPD5733	Approved
0.6939	Remote Similarity	NPD5173	Approved
0.6939	Remote Similarity	NPD7902	Approved
0.6914	Remote Similarity	NPD4224	Phase 2
0.6907	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4758	Discontinued
0.6905	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6905	Remote Similarity	NPD4243	Approved
0.6905	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5223	Approved
0.6889	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD3698	Phase 2
0.6867	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD7525	Registered
0.6848	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD5692	Phase 3
0.6837	Remote Similarity	NPD7732	Phase 3
0.6832	Remote Similarity	NPD5224	Approved
0.6832	Remote Similarity	NPD5211	Phase 2
0.6832	Remote Similarity	NPD5226	Approved
0.6832	Remote Similarity	NPD4633	Approved
0.6832	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD5364	Discontinued
0.6809	Remote Similarity	NPD4518	Approved
0.6796	Remote Similarity	NPD5739	Approved
0.6796	Remote Similarity	NPD6675	Approved
0.6796	Remote Similarity	NPD7128	Approved
0.6796	Remote Similarity	NPD6402	Approved
0.679	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5694	Approved
0.6765	Remote Similarity	NPD5174	Approved
0.6765	Remote Similarity	NPD4754	Approved
0.6765	Remote Similarity	NPD5175	Approved
0.6747	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6744	Remote Similarity	NPD4785	Approved
0.6744	Remote Similarity	NPD4784	Approved
0.6744	Remote Similarity	NPD4687	Approved
0.6707	Remote Similarity	NPD7331	Phase 2
0.6706	Remote Similarity	NPD5276	Approved
0.6702	Remote Similarity	NPD3573	Approved
0.67	Remote Similarity	NPD7638	Approved
0.6699	Remote Similarity	NPD5141	Approved
0.6698	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7320	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD5207	Approved
0.6635	Remote Similarity	NPD4767	Approved
0.6635	Remote Similarity	NPD4768	Approved
0.6634	Remote Similarity	NPD7640	Approved
0.6634	Remote Similarity	NPD7639	Approved
0.6633	Remote Similarity	NPD7900	Approved
0.6633	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6633	Remote Similarity	NPD6001	Approved
0.6604	Remote Similarity	NPD6372	Approved
0.6604	Remote Similarity	NPD6373	Approved
0.6598	Remote Similarity	NPD8035	Phase 2
0.6598	Remote Similarity	NPD8034	Phase 2
0.6591	Remote Similarity	NPD6117	Approved
0.6571	Remote Similarity	NPD5697	Approved
0.6571	Remote Similarity	NPD5701	Approved
0.6571	Remote Similarity	NPD6614	Approved
0.6571	Remote Similarity	NPD6412	Phase 2
0.6566	Remote Similarity	NPD5654	Approved
0.6552	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6883	Approved
0.6542	Remote Similarity	NPD7290	Approved
0.6542	Remote Similarity	NPD7102	Approved
0.6522	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6517	Remote Similarity	NPD6116	Phase 1
0.6509	Remote Similarity	NPD4730	Approved
0.6509	Remote Similarity	NPD4729	Approved
0.6509	Remote Similarity	NPD5128	Approved
0.6509	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD7632	Discontinued
0.6486	Remote Similarity	NPD7115	Discovery
0.6481	Remote Similarity	NPD6617	Approved
0.6481	Remote Similarity	NPD6649	Approved
0.6481	Remote Similarity	NPD8130	Phase 1
0.6481	Remote Similarity	NPD6847	Approved
0.6481	Remote Similarity	NPD6869	Approved
0.6481	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6650	Approved
0.6477	Remote Similarity	NPD5275	Approved
0.6477	Remote Similarity	NPD3703	Phase 2
0.6477	Remote Similarity	NPD7339	Approved
0.6477	Remote Similarity	NPD4190	Phase 3
0.6477	Remote Similarity	NPD6942	Approved
0.6465	Remote Similarity	NPD5282	Discontinued
0.6449	Remote Similarity	NPD6014	Approved
0.6449	Remote Similarity	NPD6012	Approved
0.6449	Remote Similarity	NPD6013	Approved
0.6444	Remote Similarity	NPD6114	Approved
0.6444	Remote Similarity	NPD6118	Approved
0.6444	Remote Similarity	NPD6115	Approved
0.6444	Remote Similarity	NPD6697	Approved
0.6442	Remote Similarity	NPD6052	Approved
0.6436	Remote Similarity	NPD5959	Approved
0.6422	Remote Similarity	NPD6882	Approved
0.6422	Remote Similarity	NPD8297	Approved
0.6413	Remote Similarity	NPD8028	Phase 2
0.6404	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6389	Remote Similarity	NPD5251	Approved
0.6389	Remote Similarity	NPD5135	Approved
0.6389	Remote Similarity	NPD5249	Phase 3
0.6389	Remote Similarity	NPD5169	Approved
0.6389	Remote Similarity	NPD5247	Approved
0.6389	Remote Similarity	NPD5248	Approved
0.6389	Remote Similarity	NPD5250	Approved
0.6364	Remote Similarity	NPD6926	Approved
0.6364	Remote Similarity	NPD6924	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