NPASS Compound

Structure

CID303613 OpenBabel06191716112D 31 34 0 0 1 0 0 0 0 0999 V2000 -5.8198 5.4576 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8189 2.0803 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2815 2.9242 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8945 3.7697 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5364 2.4740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3071 4.6131 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3567 2.9250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8444 3.7692 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2254 1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2251 0.4868 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6893 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8456 1.4631 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8445 0.4882 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6910 1.9508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -1.4637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6902 -0.9764 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3066 2.9244 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3817 2.9253 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.8194 3.7689 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6895 -0.9755 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6905 -0.0005 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3815 1.9503 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5358 0.4872 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8454 0.4877 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 -1.4642 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5361 1.4626 0.0000 C 0 0 1 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 2.5558 -1.4751 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 -2.4642 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 7 20 2 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 11 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 25 1 0 0 0 0 14 29 1 0 0 0 0 15 28 1 0 0 0 0 16 21 1 0 0 0 0 16 26 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 19 4 1 1 0 0 0 19 23 1 0 0 0 0 21 30 2 0 0 0 0 22 17 1 1 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 28 1 6 0 0 0 24 28 1 6 0 0 0 25 29 1 6 0 0 0 26 27 1 0 0 0 0 26 29 1 0 0 0 0 27 31 2 0 0 0 0 28 5 1 6 0 0 0 29 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	424.33
Volume:	482.949
LogP:	5.177
LogD:	5.603
LogS:	-5.431
# Rotatable Bonds:	5
TPSA:	34.14
# H-Bond Aceptor:	2
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.429
Synthetic Accessibility Score:	4.841
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.009
MDCK Permeability:	1.2770134162565228e-05
Pgp-inhibitor:	0.86
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.844
30% Bioavailability (F30%):	0.973

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.684
Plasma Protein Binding (PPB):	92.90584564208984%
Volume Distribution (VD):	1.379
Pgp-substrate:	1.7035540342330933%

ADMET: Metabolism

CYP1A2-inhibitor:	0.052
CYP1A2-substrate:	0.601
CYP2C19-inhibitor:	0.195
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.283
CYP2C9-substrate:	0.683
CYP2D6-inhibitor:	0.032
CYP2D6-substrate:	0.863
CYP3A4-inhibitor:	0.685
CYP3A4-substrate:	0.671

ADMET: Excretion

Clearance (CL):	5.985
Half-life (T1/2):	0.292

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.454
Drug-inuced Liver Injury (DILI):	0.543
AMES Toxicity:	0.01
Rat Oral Acute Toxicity:	0.132
Maximum Recommended Daily Dose:	0.183
Skin Sensitization:	0.648
Carcinogencity:	0.029
Eye Corrosion:	0.049
Eye Irritation:	0.24
Respiratory Toxicity:	0.927

Download Data

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

Natural Product: NPC303613

Natural Product ID:	NPC303613
*Common Name:**	24-Ethylcholesta-4,24(28)-Dien-3,6-Dione
IUPAC Name:	(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
Synonyms:
Standard InCHIKey:	QCHAAVBXLBQKTJ-FPIWNRGUSA-N
Standard InCHI:	InChI=1S/C29H44O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h7,16,18-19,22-25H,8-15,17H2,1-6H3/b20-7+/t19-,22+,23-,24+,25+,28-,29-/m1/s1
SMILES:	C/C=C(CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC(=O)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C)/C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL527206
PubChem CID:	10502463
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002031] Stigmastanes 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
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10075746]
NPO6567	Aesculus x carnea	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16768	Tortella inclinata	Species	Pottiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6567	Aesculus x carnea	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21457	Schefflera taiwaniana	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16318	Turbinaria conoides	Species	Sargassaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15720	Russula flavida	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20447	Ichthyothere rufa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18754	Agathosma capensis	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27825	Diospyros sapota	Species	Ebenaceae	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
ED50	4

Activity Type	# Activity
Cell Line	4

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	0.6	ug ml-1	PMID[529762]
NPT91	Cell Line	KB	Homo sapiens	ED50	=	5.9	ug ml-1	PMID[529762]
NPT81	Cell Line	A549	Homo sapiens	ED50	=	3.1	ug ml-1	PMID[529762]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	0.4	ug ml-1	PMID[529762]

☑ 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 NPC303613 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	175
0.1-0.2	1959
0.2-0.3	11297
0.3-0.4	13393
0.4-0.5	7456
0.5-0.6	5415
0.6-0.7	2352
0.7-0.8	525
0.8-0.85	74
0.85-0.9	19
0.9-0.95	15
0.95-1	17

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474228
0.9706	High Similarity	NPC251705
0.9701	High Similarity	NPC265782
0.9701	High Similarity	NPC35734
0.9701	High Similarity	NPC251929
0.9701	High Similarity	NPC159577
0.9701	High Similarity	NPC2634
0.9701	High Similarity	NPC307176
0.9701	High Similarity	NPC282593
0.9571	High Similarity	NPC69408
0.9565	High Similarity	NPC255021
0.9565	High Similarity	NPC309852
0.9559	High Similarity	NPC234707
0.9559	High Similarity	NPC54123
0.9559	High Similarity	NPC305501
0.9559	High Similarity	NPC115023
0.9552	High Similarity	NPC139397
0.9429	High Similarity	NPC293803
0.942	High Similarity	NPC470045
0.942	High Similarity	NPC470044
0.9412	High Similarity	NPC260040
0.9403	High Similarity	NPC20610
0.9265	High Similarity	NPC182815
0.9155	High Similarity	NPC255650
0.9054	High Similarity	NPC474509
0.9014	High Similarity	NPC474796
0.9014	High Similarity	NPC474797
0.9014	High Similarity	NPC329866
0.9	High Similarity	NPC470078
0.8971	High Similarity	NPC176107
0.8919	High Similarity	NPC90965
0.8919	High Similarity	NPC170793
0.8889	High Similarity	NPC473171
0.8857	High Similarity	NPC477856
0.8857	High Similarity	NPC214770
0.8857	High Similarity	NPC40574
0.8841	High Similarity	NPC188292
0.8841	High Similarity	NPC260474
0.8824	High Similarity	NPC323005
0.8824	High Similarity	NPC92327
0.8816	High Similarity	NPC472239
0.8806	High Similarity	NPC212210
0.8732	High Similarity	NPC5701
0.8732	High Similarity	NPC223187
0.8732	High Similarity	NPC190035
0.8714	High Similarity	NPC477857
0.8714	High Similarity	NPC256846
0.8657	High Similarity	NPC165695
0.8571	High Similarity	NPC472867
0.8571	High Similarity	NPC142253
0.8571	High Similarity	NPC320514
0.8571	High Similarity	NPC3511
0.8571	High Similarity	NPC87141
0.8571	High Similarity	NPC310992
0.8533	High Similarity	NPC470052
0.8533	High Similarity	NPC82635
0.8533	High Similarity	NPC469996
0.8529	High Similarity	NPC469662
0.8514	High Similarity	NPC469796
0.8514	High Similarity	NPC469793
0.8514	High Similarity	NPC474463
0.8507	High Similarity	NPC213152
0.8481	Intermediate Similarity	NPC29447
0.8472	Intermediate Similarity	NPC181204
0.8472	Intermediate Similarity	NPC225467
0.8451	Intermediate Similarity	NPC286814
0.8429	Intermediate Similarity	NPC475523
0.8406	Intermediate Similarity	NPC251118
0.84	Intermediate Similarity	NPC91665
0.8382	Intermediate Similarity	NPC202118
0.8382	Intermediate Similarity	NPC197238
0.8358	Intermediate Similarity	NPC127582
0.8358	Intermediate Similarity	NPC25853
0.8354	Intermediate Similarity	NPC181743
0.8354	Intermediate Similarity	NPC87552
0.8354	Intermediate Similarity	NPC16287
0.8354	Intermediate Similarity	NPC85774
0.8354	Intermediate Similarity	NPC178025
0.8354	Intermediate Similarity	NPC214043
0.8333	Intermediate Similarity	NPC193347
0.8333	Intermediate Similarity	NPC100297
0.8312	Intermediate Similarity	NPC472478
0.831	Intermediate Similarity	NPC296697
0.831	Intermediate Similarity	NPC39157
0.831	Intermediate Similarity	NPC155198
0.831	Intermediate Similarity	NPC142754
0.831	Intermediate Similarity	NPC82477
0.8289	Intermediate Similarity	NPC228911
0.8289	Intermediate Similarity	NPC115515
0.8286	Intermediate Similarity	NPC39462
0.8286	Intermediate Similarity	NPC176171
0.8286	Intermediate Similarity	NPC43300
0.8286	Intermediate Similarity	NPC189917
0.8286	Intermediate Similarity	NPC107704
0.8286	Intermediate Similarity	NPC96812
0.8286	Intermediate Similarity	NPC168824
0.8272	Intermediate Similarity	NPC93778
0.8261	Intermediate Similarity	NPC475124
0.8261	Intermediate Similarity	NPC285371
0.825	Intermediate Similarity	NPC60350
0.825	Intermediate Similarity	NPC469948
0.825	Intermediate Similarity	NPC8571
0.8243	Intermediate Similarity	NPC219232
0.8243	Intermediate Similarity	NPC211641
0.8243	Intermediate Similarity	NPC159497
0.8243	Intermediate Similarity	NPC128346
0.8235	Intermediate Similarity	NPC60565
0.8228	Intermediate Similarity	NPC41539
0.8209	Intermediate Similarity	NPC259261
0.8209	Intermediate Similarity	NPC276764
0.8209	Intermediate Similarity	NPC472304
0.8205	Intermediate Similarity	NPC147066
0.8205	Intermediate Similarity	NPC477372
0.8182	Intermediate Similarity	NPC215843
0.8182	Intermediate Similarity	NPC190211
0.8169	Intermediate Similarity	NPC220210
0.8169	Intermediate Similarity	NPC20181
0.8158	Intermediate Similarity	NPC470557
0.8148	Intermediate Similarity	NPC145879
0.8148	Intermediate Similarity	NPC474778
0.8148	Intermediate Similarity	NPC474733
0.8148	Intermediate Similarity	NPC31564
0.8148	Intermediate Similarity	NPC474732
0.8125	Intermediate Similarity	NPC237712
0.8125	Intermediate Similarity	NPC144258
0.8125	Intermediate Similarity	NPC473246
0.8116	Intermediate Similarity	NPC288253
0.8116	Intermediate Similarity	NPC32285
0.8116	Intermediate Similarity	NPC472306
0.8108	Intermediate Similarity	NPC474488
0.8101	Intermediate Similarity	NPC469804
0.8101	Intermediate Similarity	NPC469805
0.8101	Intermediate Similarity	NPC321289
0.8101	Intermediate Similarity	NPC327969
0.8072	Intermediate Similarity	NPC262043
0.806	Intermediate Similarity	NPC56905
0.806	Intermediate Similarity	NPC266295
0.806	Intermediate Similarity	NPC27610
0.806	Intermediate Similarity	NPC30215
0.806	Intermediate Similarity	NPC94991
0.8052	Intermediate Similarity	NPC105197
0.8049	Intermediate Similarity	NPC58063
0.8049	Intermediate Similarity	NPC476293
0.8049	Intermediate Similarity	NPC136948
0.8049	Intermediate Similarity	NPC475740
0.8026	Intermediate Similarity	NPC1254
0.8025	Intermediate Similarity	NPC472940
0.8025	Intermediate Similarity	NPC472931
0.8025	Intermediate Similarity	NPC11711
0.8	Intermediate Similarity	NPC474790
0.8	Intermediate Similarity	NPC470046
0.8	Intermediate Similarity	NPC3856
0.8	Intermediate Similarity	NPC470047
0.8	Intermediate Similarity	NPC474976
0.8	Intermediate Similarity	NPC279639
0.8	Intermediate Similarity	NPC168188
0.8	Intermediate Similarity	NPC473902
0.8	Intermediate Similarity	NPC470015
0.7975	Intermediate Similarity	NPC38350
0.7975	Intermediate Similarity	NPC278459
0.7975	Intermediate Similarity	NPC4166
0.7975	Intermediate Similarity	NPC201912
0.7973	Intermediate Similarity	NPC304983
0.7973	Intermediate Similarity	NPC474562
0.7971	Intermediate Similarity	NPC475795
0.7949	Intermediate Similarity	NPC472490
0.7949	Intermediate Similarity	NPC477371
0.7927	Intermediate Similarity	NPC222613
0.7927	Intermediate Similarity	NPC195640
0.7927	Intermediate Similarity	NPC475022
0.7927	Intermediate Similarity	NPC118648
0.7922	Intermediate Similarity	NPC472300
0.7917	Intermediate Similarity	NPC290350
0.7917	Intermediate Similarity	NPC4370
0.791	Intermediate Similarity	NPC49575
0.791	Intermediate Similarity	NPC55004
0.791	Intermediate Similarity	NPC267626
0.791	Intermediate Similarity	NPC230823
0.7901	Intermediate Similarity	NPC227064
0.7901	Intermediate Similarity	NPC59453
0.7901	Intermediate Similarity	NPC329043
0.7901	Intermediate Similarity	NPC221758
0.7901	Intermediate Similarity	NPC320801
0.7901	Intermediate Similarity	NPC321187
0.7901	Intermediate Similarity	NPC472265
0.7901	Intermediate Similarity	NPC82902
0.7901	Intermediate Similarity	NPC161423
0.7901	Intermediate Similarity	NPC58841
0.7895	Intermediate Similarity	NPC65650
0.7895	Intermediate Similarity	NPC476346
0.7882	Intermediate Similarity	NPC218301
0.7882	Intermediate Similarity	NPC272746
0.7875	Intermediate Similarity	NPC260956
0.7875	Intermediate Similarity	NPC469799
0.7875	Intermediate Similarity	NPC311092
0.7875	Intermediate Similarity	NPC469806
0.7867	Intermediate Similarity	NPC52667
0.7867	Intermediate Similarity	NPC130016
0.7867	Intermediate Similarity	NPC109576
0.7867	Intermediate Similarity	NPC180015

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 NPC303613 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	167
0.1-0.2	2040
0.2-0.3	4574
0.3-0.4	1689
0.4-0.5	320
0.5-0.6	125
0.6-0.7	139
0.7-0.8	72
0.8-0.85	14
0.85-0.9	4
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9701	High Similarity	NPD4691	Approved
0.9701	High Similarity	NPD4747	Approved
0.9552	High Similarity	NPD4137	Phase 3
0.9286	High Similarity	NPD4058	Approved
0.9286	High Similarity	NPD5733	Approved
0.9014	High Similarity	NPD4687	Approved
0.9	High Similarity	NPD5276	Approved
0.8841	High Similarity	NPD3621	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD4221	Approved
0.8333	Intermediate Similarity	NPD4223	Phase 3
0.825	Intermediate Similarity	NPD5329	Approved
0.8125	Intermediate Similarity	NPD4197	Approved
0.8	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7952	Intermediate Similarity	NPD6672	Approved
0.7952	Intermediate Similarity	NPD5737	Approved
0.7927	Intermediate Similarity	NPD4688	Approved
0.7927	Intermediate Similarity	NPD4693	Phase 3
0.7927	Intermediate Similarity	NPD7334	Approved
0.7927	Intermediate Similarity	NPD4690	Approved
0.7927	Intermediate Similarity	NPD6409	Approved
0.7927	Intermediate Similarity	NPD6684	Approved
0.7927	Intermediate Similarity	NPD4138	Approved
0.7927	Intermediate Similarity	NPD5205	Approved
0.7927	Intermediate Similarity	NPD7146	Approved
0.7927	Intermediate Similarity	NPD4689	Approved
0.7927	Intermediate Similarity	NPD7521	Approved
0.7927	Intermediate Similarity	NPD5330	Approved
0.7927	Intermediate Similarity	NPD5690	Phase 2
0.7901	Intermediate Similarity	NPD4786	Approved
0.7901	Intermediate Similarity	NPD3666	Approved
0.7901	Intermediate Similarity	NPD3133	Approved
0.7901	Intermediate Similarity	NPD3665	Phase 1
0.7882	Intermediate Similarity	NPD6079	Approved
0.7857	Intermediate Similarity	NPD6673	Approved
0.7857	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD6904	Approved
0.7857	Intermediate Similarity	NPD6080	Approved
0.7821	Intermediate Similarity	NPD3617	Approved
0.775	Intermediate Similarity	NPD8028	Phase 2
0.7738	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD6903	Approved
0.7738	Intermediate Similarity	NPD5208	Approved
0.7722	Intermediate Similarity	NPD4195	Approved
0.7711	Intermediate Similarity	NPD4694	Approved
0.7711	Intermediate Similarity	NPD6098	Approved
0.7711	Intermediate Similarity	NPD3618	Phase 1
0.7711	Intermediate Similarity	NPD5280	Approved
0.7711	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD3667	Approved
0.7647	Intermediate Similarity	NPD4753	Phase 2
0.7625	Intermediate Similarity	NPD4695	Discontinued
0.7536	Intermediate Similarity	NPD287	Approved
0.75	Intermediate Similarity	NPD5279	Phase 3
0.7471	Intermediate Similarity	NPD5693	Phase 1
0.7471	Intermediate Similarity	NPD6050	Approved
0.747	Intermediate Similarity	NPD3668	Phase 3
0.7416	Intermediate Similarity	NPD4629	Approved
0.7416	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD5210	Approved
0.7386	Intermediate Similarity	NPD4202	Approved
0.7356	Intermediate Similarity	NPD5692	Phase 3
0.7356	Intermediate Similarity	NPD5207	Approved
0.7349	Intermediate Similarity	NPD4788	Approved
0.7333	Intermediate Similarity	NPD5221	Approved
0.7333	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7303	Intermediate Similarity	NPD6001	Approved
0.7294	Intermediate Similarity	NPD4519	Discontinued
0.7294	Intermediate Similarity	NPD4623	Approved
0.7273	Intermediate Similarity	NPD5281	Approved
0.7273	Intermediate Similarity	NPD5284	Approved
0.7273	Intermediate Similarity	NPD5694	Approved
0.7253	Intermediate Similarity	NPD5173	Approved
0.7253	Intermediate Similarity	NPD6084	Phase 2
0.7253	Intermediate Similarity	NPD6083	Phase 2
0.7209	Intermediate Similarity	NPD3573	Approved
0.7191	Intermediate Similarity	NPD6399	Phase 3
0.7159	Intermediate Similarity	NPD4096	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7108	Intermediate Similarity	NPD4692	Approved
0.7108	Intermediate Similarity	NPD4139	Approved
0.7097	Intermediate Similarity	NPD5286	Approved
0.7097	Intermediate Similarity	NPD4696	Approved
0.7097	Intermediate Similarity	NPD5285	Approved
0.7065	Intermediate Similarity	NPD4755	Approved
0.7051	Intermediate Similarity	NPD4243	Approved
0.7033	Intermediate Similarity	NPD5695	Phase 3
0.7021	Intermediate Similarity	NPD5223	Approved
0.7	Intermediate Similarity	NPD5133	Approved
0.6989	Remote Similarity	NPD5696	Approved
0.6947	Remote Similarity	NPD5225	Approved
0.6947	Remote Similarity	NPD5226	Approved
0.6947	Remote Similarity	NPD5224	Approved
0.6947	Remote Similarity	NPD4633	Approved
0.6947	Remote Similarity	NPD5211	Phase 2
0.6947	Remote Similarity	NPD5091	Approved
0.6932	Remote Similarity	NPD4518	Approved
0.6915	Remote Similarity	NPD4700	Approved
0.6889	Remote Similarity	NPD7515	Phase 2
0.6875	Remote Similarity	NPD4785	Approved
0.6875	Remote Similarity	NPD5175	Approved
0.6875	Remote Similarity	NPD6052	Approved
0.6875	Remote Similarity	NPD4784	Approved
0.6875	Remote Similarity	NPD5174	Approved
0.6854	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD5654	Approved
0.6837	Remote Similarity	NPD6614	Approved
0.6824	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5141	Approved
0.679	Remote Similarity	NPD6942	Approved
0.679	Remote Similarity	NPD7339	Approved
0.6768	Remote Similarity	NPD6881	Approved
0.6768	Remote Similarity	NPD6899	Approved
0.6739	Remote Similarity	NPD7748	Approved
0.6739	Remote Similarity	NPD7900	Approved
0.6739	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6737	Remote Similarity	NPD6404	Discontinued
0.6735	Remote Similarity	NPD6675	Approved
0.6735	Remote Similarity	NPD6402	Approved
0.6735	Remote Similarity	NPD7128	Approved
0.6735	Remote Similarity	NPD5739	Approved
0.6702	Remote Similarity	NPD5959	Approved
0.6701	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD5697	Approved
0.6634	Remote Similarity	NPD7102	Approved
0.6634	Remote Similarity	NPD7290	Approved
0.6634	Remote Similarity	NPD6883	Approved
0.6623	Remote Similarity	NPD7331	Phase 2
0.66	Remote Similarity	NPD5168	Approved
0.66	Remote Similarity	NPD4729	Approved
0.66	Remote Similarity	NPD6011	Approved
0.66	Remote Similarity	NPD4730	Approved
0.66	Remote Similarity	NPD7320	Approved
0.66	Remote Similarity	NPD5128	Approved
0.6596	Remote Similarity	NPD7614	Phase 1
0.6596	Remote Similarity	NPD7732	Phase 3
0.6591	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD4190	Phase 3
0.6585	Remote Similarity	NPD5275	Approved
0.6569	Remote Similarity	NPD6650	Approved
0.6569	Remote Similarity	NPD6649	Approved
0.6569	Remote Similarity	NPD6847	Approved
0.6569	Remote Similarity	NPD6869	Approved
0.6569	Remote Similarity	NPD6617	Approved
0.6569	Remote Similarity	NPD8130	Phase 1
0.6566	Remote Similarity	NPD4768	Approved
0.6566	Remote Similarity	NPD6008	Approved
0.6566	Remote Similarity	NPD4767	Approved
0.6559	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD6014	Approved
0.6535	Remote Similarity	NPD6012	Approved
0.6535	Remote Similarity	NPD6373	Approved
0.6535	Remote Similarity	NPD6013	Approved
0.6535	Remote Similarity	NPD6372	Approved
0.6526	Remote Similarity	NPD7902	Approved
0.6526	Remote Similarity	NPD3495	Discontinued
0.6506	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD6882	Approved
0.6505	Remote Similarity	NPD8297	Approved
0.65	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.65	Remote Similarity	NPD6939	Phase 2
0.65	Remote Similarity	NPD6412	Phase 2
0.65	Remote Similarity	NPD5701	Approved
0.6471	Remote Similarity	NPD5250	Approved
0.6471	Remote Similarity	NPD5169	Approved
0.6471	Remote Similarity	NPD5247	Approved
0.6471	Remote Similarity	NPD5248	Approved
0.6471	Remote Similarity	NPD5251	Approved
0.6471	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4634	Approved
0.6471	Remote Similarity	NPD5249	Phase 3
0.6471	Remote Similarity	NPD5135	Approved
0.6456	Remote Similarity	NPD5360	Phase 3
0.6456	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD5215	Approved
0.6408	Remote Similarity	NPD5216	Approved
0.6408	Remote Similarity	NPD5217	Approved
0.6408	Remote Similarity	NPD5127	Approved
0.6408	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD1694	Approved
0.6395	Remote Similarity	NPD7525	Registered
0.6375	Remote Similarity	NPD6922	Approved
0.6375	Remote Similarity	NPD6923	Approved
0.6353	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD6868	Approved
0.6304	Remote Similarity	NPD6051	Approved
0.6296	Remote Similarity	NPD7144	Approved
0.6296	Remote Similarity	NPD4789	Approved
0.6296	Remote Similarity	NPD7143	Approved
0.6289	Remote Similarity	NPD7638	Approved
0.6286	Remote Similarity	NPD4632	Approved
0.6282	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD7341	Phase 2
0.6277	Remote Similarity	NPD7631	Approved
0.6265	Remote Similarity	NPD6924	Approved
0.6265	Remote Similarity	NPD6926	Approved
0.6262	Remote Similarity	NPD7115	Discovery
0.6226	Remote Similarity	NPD5167	Approved
0.6224	Remote Similarity	NPD7639	Approved
0.6224	Remote Similarity	NPD7640	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