NPASS Compound

Structure

NPC305501 OpenBabel07101718322D 29 32 0 0 1 0 0 0 0 0999 V2000 1.5417 4.0385 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1816 5.7327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8363 2.9680 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 2.1913 2.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1890 3.5032 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 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1369 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4980 4.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 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 1.8508 4.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8581 2.7601 0.0000 C 0 0 2 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 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8289 5.1974 0.0000 C 0 0 0 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 2.5981 1.5000 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 3.1379 6.1485 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 17 1 0 0 0 0 6 11 1 0 0 0 0 6 18 1 0 0 0 0 7 8 1 0 0 0 0 7 19 1 0 0 0 0 9 10 1 0 0 0 0 9 22 1 0 0 0 0 10 23 1 0 0 0 0 11 25 1 0 0 0 0 12 14 2 0 0 0 0 12 20 1 0 0 0 0 13 15 1 0 0 0 0 13 24 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 19 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 3 1 1 0 0 0 18 22 1 0 0 0 0 19 26 1 1 0 0 0 20 28 2 0 0 0 0 21 8 1 6 0 0 0 21 23 1 0 0 0 0 21 24 1 0 0 0 0 22 27 1 1 0 0 0 23 27 1 1 0 0 0 24 26 1 1 0 0 0 25 29 2 0 0 0 0 26 4 1 1 0 0 0 27 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	398.32
Volume:	450.993
LogP:	6.3
LogD:	5.553
LogS:	-5.597
# 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:	0.521
Synthetic Accessibility Score:	4.401
Fsp3:	0.852
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:	-4.778
MDCK Permeability:	2.4564526029280387e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.966
30% Bioavailability (F30%):	0.963

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.202
Plasma Protein Binding (PPB):	92.89104461669922%
Volume Distribution (VD):	1.126
Pgp-substrate:	1.4850571155548096%

ADMET: Metabolism

CYP1A2-inhibitor:	0.268
CYP1A2-substrate:	0.302
CYP2C19-inhibitor:	0.551
CYP2C19-substrate:	0.912
CYP2C9-inhibitor:	0.584
CYP2C9-substrate:	0.132
CYP2D6-inhibitor:	0.481
CYP2D6-substrate:	0.347
CYP3A4-inhibitor:	0.954
CYP3A4-substrate:	0.815

ADMET: Excretion

Clearance (CL):	10.961
Half-life (T1/2):	0.336

ADMET: Toxicity

hERG Blockers:	0.549
Human Hepatotoxicity (H-HT):	0.536
Drug-inuced Liver Injury (DILI):	0.812
AMES Toxicity:	0.012
Rat Oral Acute Toxicity:	0.696
Maximum Recommended Daily Dose:	0.634
Skin Sensitization:	0.959
Carcinogencity:	0.648
Eye Corrosion:	0.322
Eye Irritation:	0.153
Respiratory Toxicity:	0.97

Download Data

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

Natural Product: NPC305501

Natural Product ID:	NPC305501
*Common Name:**	(5S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-17-[(2R)-6-Methyl-5-Oxoheptan-2-Yl]-4,5,6,7,8,9,11,12,14,15,16,17-Dodecahydrocyclopenta[A]Phenanthren-3-One
IUPAC Name:	(5S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-oxoheptan-2-yl]-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	FFSLFGDAYRVXAQ-COIRZXSFSA-N
Standard InCHI:	InChI=1S/C27H42O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h12,14,17-19,21-24H,6-11,13,15-16H2,1-5H3/t18-,19+,21+,22-,23+,24+,26+,27-/m1/s1
SMILES:	CC(C)C(=O)CC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4CC(=O)C=C[C@]4(C)[C@H]3CC[C@]12C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL465614
PubChem CID:	44584339
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001445] Bile acids, 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
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10843584]
NPO33357	lemnalia carvicorni	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15497934]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	PMID[30407007]
NPO25976	Dendronephthya gigantea	Species	Nephtheidae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT139	Cell Line	HT-29	Homo sapiens	ED50	=	9.03	uM	PMID[524134]
NPT168	Cell Line	P388	Mus musculus	ED50	=	8.93	uM	PMID[524134]

☑ 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 NPC305501 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	172
0.1-0.2	2103
0.2-0.3	12647
0.3-0.4	12581
0.4-0.5	7864
0.5-0.6	4999
0.6-0.7	1844
0.7-0.8	412
0.8-0.85	36
0.85-0.9	13
0.9-0.95	20
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
0.9701	High Similarity	NPC234707
0.9559	High Similarity	NPC303613
0.9559	High Similarity	NPC251705
0.9559	High Similarity	NPC474228
0.9429	High Similarity	NPC69408
0.942	High Similarity	NPC309852
0.942	High Similarity	NPC255021
0.9412	High Similarity	NPC54123
0.9412	High Similarity	NPC115023
0.9286	High Similarity	NPC255650
0.9286	High Similarity	NPC293803
0.9275	High Similarity	NPC470045
0.9275	High Similarity	NPC470044
0.9265	High Similarity	NPC159577
0.9265	High Similarity	NPC2634
0.9265	High Similarity	NPC35734
0.9265	High Similarity	NPC307176
0.9265	High Similarity	NPC265782
0.9265	High Similarity	NPC282593
0.9265	High Similarity	NPC251929
0.9118	High Similarity	NPC139397
0.9118	High Similarity	NPC182815
0.8986	High Similarity	NPC40574
0.8986	High Similarity	NPC260040
0.8971	High Similarity	NPC20610
0.8955	High Similarity	NPC323005
0.8919	High Similarity	NPC474509
0.8873	High Similarity	NPC474796
0.8873	High Similarity	NPC474797
0.8873	High Similarity	NPC329866
0.8857	High Similarity	NPC5701
0.8857	High Similarity	NPC470078
0.8824	High Similarity	NPC176107
0.875	High Similarity	NPC473171
0.8696	High Similarity	NPC188292
0.8696	High Similarity	NPC260474
0.8684	High Similarity	NPC100297
0.8676	High Similarity	NPC92327
0.8592	High Similarity	NPC223187
0.8592	High Similarity	NPC225467
0.8571	High Similarity	NPC256846
0.8533	High Similarity	NPC90965
0.8533	High Similarity	NPC170793
0.8451	Intermediate Similarity	NPC477856
0.8451	Intermediate Similarity	NPC214770
0.8442	Intermediate Similarity	NPC472239
0.8429	Intermediate Similarity	NPC87141
0.84	Intermediate Similarity	NPC470052
0.84	Intermediate Similarity	NPC82635
0.8382	Intermediate Similarity	NPC469662
0.8382	Intermediate Similarity	NPC212210
0.8378	Intermediate Similarity	NPC469793
0.8378	Intermediate Similarity	NPC469796
0.8378	Intermediate Similarity	NPC474463
0.8354	Intermediate Similarity	NPC29447
0.8333	Intermediate Similarity	NPC181204
0.8333	Intermediate Similarity	NPC190035
0.831	Intermediate Similarity	NPC477857
0.8267	Intermediate Similarity	NPC470557
0.8267	Intermediate Similarity	NPC91665
0.8261	Intermediate Similarity	NPC251118
0.8235	Intermediate Similarity	NPC202118
0.8235	Intermediate Similarity	NPC197238
0.8235	Intermediate Similarity	NPC165695
0.8205	Intermediate Similarity	NPC320514
0.8205	Intermediate Similarity	NPC3511
0.8205	Intermediate Similarity	NPC142253
0.8205	Intermediate Similarity	NPC472867
0.8169	Intermediate Similarity	NPC310992
0.8158	Intermediate Similarity	NPC469996
0.8148	Intermediate Similarity	NPC93778
0.8143	Intermediate Similarity	NPC176171
0.8088	Intermediate Similarity	NPC213152
0.8056	Intermediate Similarity	NPC286814
0.8052	Intermediate Similarity	NPC190211
0.8028	Intermediate Similarity	NPC20181
0.8028	Intermediate Similarity	NPC220210
0.8028	Intermediate Similarity	NPC475523
0.8	Intermediate Similarity	NPC16287
0.8	Intermediate Similarity	NPC87552
0.8	Intermediate Similarity	NPC214043
0.8	Intermediate Similarity	NPC178025
0.8	Intermediate Similarity	NPC181743
0.8	Intermediate Similarity	NPC85774
0.7975	Intermediate Similarity	NPC193347
0.7975	Intermediate Similarity	NPC469805
0.7975	Intermediate Similarity	NPC469804
0.7971	Intermediate Similarity	NPC472306
0.7971	Intermediate Similarity	NPC288253
0.7952	Intermediate Similarity	NPC262043
0.7949	Intermediate Similarity	NPC469797
0.7949	Intermediate Similarity	NPC469798
0.7949	Intermediate Similarity	NPC472478
0.7941	Intermediate Similarity	NPC25853
0.7941	Intermediate Similarity	NPC127582
0.7927	Intermediate Similarity	NPC58063
0.7927	Intermediate Similarity	NPC476293
0.7922	Intermediate Similarity	NPC105197
0.7922	Intermediate Similarity	NPC115515
0.7922	Intermediate Similarity	NPC228911
0.7917	Intermediate Similarity	NPC39157
0.7917	Intermediate Similarity	NPC155198
0.7917	Intermediate Similarity	NPC82477
0.7917	Intermediate Similarity	NPC142754
0.7917	Intermediate Similarity	NPC296697
0.7901	Intermediate Similarity	NPC469948
0.7901	Intermediate Similarity	NPC60350
0.7901	Intermediate Similarity	NPC8571
0.7895	Intermediate Similarity	NPC1254
0.7887	Intermediate Similarity	NPC168824
0.7887	Intermediate Similarity	NPC43300
0.7887	Intermediate Similarity	NPC39462
0.7887	Intermediate Similarity	NPC96812
0.7887	Intermediate Similarity	NPC189917
0.7887	Intermediate Similarity	NPC107704
0.7875	Intermediate Similarity	NPC474790
0.7875	Intermediate Similarity	NPC279639
0.7875	Intermediate Similarity	NPC474976
0.7875	Intermediate Similarity	NPC41539
0.7875	Intermediate Similarity	NPC3856
0.7867	Intermediate Similarity	NPC159497
0.7867	Intermediate Similarity	NPC219232
0.7867	Intermediate Similarity	NPC128346
0.7867	Intermediate Similarity	NPC211641
0.7857	Intermediate Similarity	NPC475124
0.7857	Intermediate Similarity	NPC285371
0.7848	Intermediate Similarity	NPC147066
0.7848	Intermediate Similarity	NPC477372
0.7826	Intermediate Similarity	NPC60565
0.7821	Intermediate Similarity	NPC215843
0.7805	Intermediate Similarity	NPC145879
0.7805	Intermediate Similarity	NPC474733
0.7805	Intermediate Similarity	NPC118648
0.7805	Intermediate Similarity	NPC31564
0.7805	Intermediate Similarity	NPC222613
0.7805	Intermediate Similarity	NPC474732
0.7805	Intermediate Similarity	NPC475022
0.7805	Intermediate Similarity	NPC474778
0.7794	Intermediate Similarity	NPC472304
0.7794	Intermediate Similarity	NPC276764
0.7794	Intermediate Similarity	NPC259261
0.7778	Intermediate Similarity	NPC144258
0.7778	Intermediate Similarity	NPC237712
0.7778	Intermediate Similarity	NPC473246
0.7765	Intermediate Similarity	NPC218301
0.7765	Intermediate Similarity	NPC272746
0.7763	Intermediate Similarity	NPC476346
0.7761	Intermediate Similarity	NPC115385
0.775	Intermediate Similarity	NPC327969
0.775	Intermediate Similarity	NPC321289
0.775	Intermediate Similarity	NPC469806
0.775	Intermediate Similarity	NPC469799
0.7738	Intermediate Similarity	NPC285982
0.7733	Intermediate Similarity	NPC474488
0.7733	Intermediate Similarity	NPC52667
0.7722	Intermediate Similarity	NPC469637
0.7722	Intermediate Similarity	NPC476809
0.7714	Intermediate Similarity	NPC32285
0.7711	Intermediate Similarity	NPC475740
0.7711	Intermediate Similarity	NPC136948
0.7711	Intermediate Similarity	NPC163016
0.7711	Intermediate Similarity	NPC75315
0.7683	Intermediate Similarity	NPC472940
0.7683	Intermediate Similarity	NPC11711
0.7683	Intermediate Similarity	NPC472931
0.7681	Intermediate Similarity	NPC270042
0.7674	Intermediate Similarity	NPC474736
0.7674	Intermediate Similarity	NPC474807
0.7654	Intermediate Similarity	NPC470046
0.7654	Intermediate Similarity	NPC470015
0.7654	Intermediate Similarity	NPC470047
0.7654	Intermediate Similarity	NPC168188
0.7647	Intermediate Similarity	NPC94991
0.7647	Intermediate Similarity	NPC60772
0.7647	Intermediate Similarity	NPC30215
0.7647	Intermediate Similarity	NPC266295
0.7647	Intermediate Similarity	NPC27610
0.7647	Intermediate Similarity	NPC56905
0.7647	Intermediate Similarity	NPC311852
0.7625	Intermediate Similarity	NPC38350
0.7625	Intermediate Similarity	NPC4166
0.7625	Intermediate Similarity	NPC201912
0.7625	Intermediate Similarity	NPC278459
0.7612	Intermediate Similarity	NPC143597
0.7612	Intermediate Similarity	NPC151464
0.7606	Intermediate Similarity	NPC473902
0.76	Intermediate Similarity	NPC474562
0.76	Intermediate Similarity	NPC304983
0.7595	Intermediate Similarity	NPC472490
0.7595	Intermediate Similarity	NPC477371
0.759	Intermediate Similarity	NPC195640
0.7586	Intermediate Similarity	NPC294266
0.7571	Intermediate Similarity	NPC475795
0.7564	Intermediate Similarity	NPC472300
0.7561	Intermediate Similarity	NPC321187
0.7561	Intermediate Similarity	NPC82902
0.7561	Intermediate Similarity	NPC221758
0.7561	Intermediate Similarity	NPC472265
0.7561	Intermediate Similarity	NPC320801
0.7561	Intermediate Similarity	NPC58841

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 NPC305501 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	2210
0.2-0.3	4612
0.3-0.4	1514
0.4-0.5	302
0.5-0.6	131
0.6-0.7	138
0.7-0.8	71
0.8-0.85	3
0.85-0.9	3
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9265	High Similarity	NPD4747	Approved
0.9265	High Similarity	NPD4691	Approved
0.9143	High Similarity	NPD4058	Approved
0.9118	High Similarity	NPD4137	Phase 3
0.8873	High Similarity	NPD5733	Approved
0.8873	High Similarity	NPD4687	Approved
0.8592	High Similarity	NPD5276	Approved
0.8429	Intermediate Similarity	NPD3621	Clinical (unspecified phase)
0.7975	Intermediate Similarity	NPD4223	Phase 3
0.7975	Intermediate Similarity	NPD4221	Approved
0.7901	Intermediate Similarity	NPD5329	Approved
0.7875	Intermediate Similarity	NPD3527	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD5690	Phase 2
0.7778	Intermediate Similarity	NPD4197	Approved
0.7765	Intermediate Similarity	NPD6079	Approved
0.7692	Intermediate Similarity	NPD3617	Approved
0.7625	Intermediate Similarity	NPD8028	Phase 2
0.7619	Intermediate Similarity	NPD6672	Approved
0.7619	Intermediate Similarity	NPD5737	Approved
0.7595	Intermediate Similarity	NPD4195	Approved
0.759	Intermediate Similarity	NPD7334	Approved
0.759	Intermediate Similarity	NPD5330	Approved
0.759	Intermediate Similarity	NPD7146	Approved
0.759	Intermediate Similarity	NPD4138	Approved
0.759	Intermediate Similarity	NPD4690	Approved
0.759	Intermediate Similarity	NPD4693	Phase 3
0.759	Intermediate Similarity	NPD7521	Approved
0.759	Intermediate Similarity	NPD6409	Approved
0.759	Intermediate Similarity	NPD4688	Approved
0.759	Intermediate Similarity	NPD4689	Approved
0.759	Intermediate Similarity	NPD6684	Approved
0.759	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.759	Intermediate Similarity	NPD5205	Approved
0.7561	Intermediate Similarity	NPD4786	Approved
0.7561	Intermediate Similarity	NPD3665	Phase 1
0.7561	Intermediate Similarity	NPD3666	Approved
0.7561	Intermediate Similarity	NPD3133	Approved
0.7529	Intermediate Similarity	NPD6904	Approved
0.7529	Intermediate Similarity	NPD5328	Approved
0.7529	Intermediate Similarity	NPD6673	Approved
0.7529	Intermediate Similarity	NPD6080	Approved
0.7412	Intermediate Similarity	NPD6903	Approved
0.7412	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD5208	Approved
0.7381	Intermediate Similarity	NPD5280	Approved
0.7381	Intermediate Similarity	NPD3618	Phase 1
0.7381	Intermediate Similarity	NPD4694	Approved
0.7381	Intermediate Similarity	NPD6098	Approved
0.7326	Intermediate Similarity	NPD4753	Phase 2
0.7317	Intermediate Similarity	NPD3667	Approved
0.7303	Intermediate Similarity	NPD5210	Approved
0.7303	Intermediate Similarity	NPD4629	Approved
0.7284	Intermediate Similarity	NPD4695	Discontinued
0.7241	Intermediate Similarity	NPD5207	Approved
0.7222	Intermediate Similarity	NPD5221	Approved
0.7222	Intermediate Similarity	NPD5222	Approved
0.7222	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7176	Intermediate Similarity	NPD4519	Discontinued
0.7176	Intermediate Similarity	NPD5279	Phase 3
0.7176	Intermediate Similarity	NPD4623	Approved
0.7159	Intermediate Similarity	NPD5693	Phase 1
0.7159	Intermediate Similarity	NPD6050	Approved
0.7159	Intermediate Similarity	NPD5284	Approved
0.7159	Intermediate Similarity	NPD5281	Approved
0.7159	Intermediate Similarity	NPD5694	Approved
0.7143	Intermediate Similarity	NPD5173	Approved
0.7143	Intermediate Similarity	NPD3668	Phase 3
0.7143	Intermediate Similarity	NPD287	Approved
0.7111	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD3573	Approved
0.7079	Intermediate Similarity	NPD4202	Approved
0.7045	Intermediate Similarity	NPD5692	Phase 3
0.7024	Intermediate Similarity	NPD4788	Approved
0.7	Intermediate Similarity	NPD6001	Approved
0.6989	Remote Similarity	NPD4696	Approved
0.6989	Remote Similarity	NPD5286	Approved
0.6989	Remote Similarity	NPD5285	Approved
0.6988	Remote Similarity	NPD4692	Approved
0.6988	Remote Similarity	NPD4139	Approved
0.6957	Remote Similarity	NPD6084	Phase 2
0.6957	Remote Similarity	NPD6083	Phase 2
0.6915	Remote Similarity	NPD5223	Approved
0.6889	Remote Similarity	NPD6399	Phase 3
0.6889	Remote Similarity	NPD5133	Approved
0.6854	Remote Similarity	NPD4096	Approved
0.6848	Remote Similarity	NPD4697	Phase 3
0.6842	Remote Similarity	NPD4633	Approved
0.6842	Remote Similarity	NPD5211	Phase 2
0.6842	Remote Similarity	NPD5226	Approved
0.6842	Remote Similarity	NPD5224	Approved
0.6842	Remote Similarity	NPD5091	Approved
0.6842	Remote Similarity	NPD5225	Approved
0.6818	Remote Similarity	NPD4518	Approved
0.6813	Remote Similarity	NPD5769	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD4755	Approved
0.6771	Remote Similarity	NPD5175	Approved
0.6771	Remote Similarity	NPD5174	Approved
0.675	Remote Similarity	NPD4784	Approved
0.675	Remote Similarity	NPD4785	Approved
0.6742	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD5654	Approved
0.6739	Remote Similarity	NPD5695	Phase 3
0.6735	Remote Similarity	NPD6614	Approved
0.6709	Remote Similarity	NPD4243	Approved
0.6702	Remote Similarity	NPD5696	Approved
0.6701	Remote Similarity	NPD5141	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD6899	Approved
0.6632	Remote Similarity	NPD4700	Approved
0.6598	Remote Similarity	NPD6052	Approved
0.6596	Remote Similarity	NPD5959	Approved
0.6593	Remote Similarity	NPD7515	Phase 2
0.6566	Remote Similarity	NPD5697	Approved
0.6538	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5360	Phase 3
0.6535	Remote Similarity	NPD7102	Approved
0.6535	Remote Similarity	NPD6883	Approved
0.6535	Remote Similarity	NPD7290	Approved
0.6512	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5168	Approved
0.65	Remote Similarity	NPD4729	Approved
0.65	Remote Similarity	NPD4730	Approved
0.65	Remote Similarity	NPD6011	Approved
0.6489	Remote Similarity	NPD7614	Phase 1
0.6489	Remote Similarity	NPD7732	Phase 3
0.6477	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD6847	Approved
0.6471	Remote Similarity	NPD6649	Approved
0.6471	Remote Similarity	NPD6869	Approved
0.6471	Remote Similarity	NPD6617	Approved
0.6471	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD6650	Approved
0.6465	Remote Similarity	NPD5739	Approved
0.6465	Remote Similarity	NPD7128	Approved
0.6465	Remote Similarity	NPD6675	Approved
0.6465	Remote Similarity	NPD6402	Approved
0.6463	Remote Similarity	NPD6942	Approved
0.6463	Remote Similarity	NPD7339	Approved
0.6458	Remote Similarity	NPD6404	Discontinued
0.6452	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7900	Approved
0.6452	Remote Similarity	NPD7748	Approved
0.6436	Remote Similarity	NPD6014	Approved
0.6436	Remote Similarity	NPD6012	Approved
0.6436	Remote Similarity	NPD6013	Approved
0.6429	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD4754	Approved
0.6421	Remote Similarity	NPD3495	Discontinued
0.6408	Remote Similarity	NPD8297	Approved
0.6408	Remote Similarity	NPD6882	Approved
0.6375	Remote Similarity	NPD4789	Approved
0.6373	Remote Similarity	NPD5251	Approved
0.6373	Remote Similarity	NPD5169	Approved
0.6373	Remote Similarity	NPD5250	Approved
0.6373	Remote Similarity	NPD4634	Approved
0.6373	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD5248	Approved
0.6373	Remote Similarity	NPD5249	Phase 3
0.6373	Remote Similarity	NPD5135	Approved
0.6373	Remote Similarity	NPD5247	Approved
0.6364	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD5128	Approved
0.6337	Remote Similarity	NPD7320	Approved
0.6311	Remote Similarity	NPD5127	Approved
0.6311	Remote Similarity	NPD5217	Approved
0.6311	Remote Similarity	NPD5216	Approved
0.6311	Remote Similarity	NPD5215	Approved
0.63	Remote Similarity	NPD6008	Approved
0.63	Remote Similarity	NPD4768	Approved
0.63	Remote Similarity	NPD4767	Approved
0.6296	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6081	Approved
0.6296	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6282	Remote Similarity	NPD4224	Phase 2
0.6282	Remote Similarity	NPD7331	Phase 2
0.6275	Remote Similarity	NPD6373	Approved
0.6275	Remote Similarity	NPD6372	Approved
0.6265	Remote Similarity	NPD4190	Phase 3
0.6265	Remote Similarity	NPD5275	Approved
0.625	Remote Similarity	NPD7902	Approved
0.6238	Remote Similarity	NPD6412	Phase 2
0.6238	Remote Similarity	NPD5701	Approved
0.6226	Remote Similarity	NPD6868	Approved
0.619	Remote Similarity	NPD4632	Approved
0.619	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD7143	Approved
0.6173	Remote Similarity	NPD7144	Approved
0.6173	Remote Similarity	NPD4245	Approved
0.6173	Remote Similarity	NPD4244	Approved
0.6173	Remote Similarity	NPD6938	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD6939	Phase 2
0.617	Remote Similarity	NPD7631	Approved
0.6168	Remote Similarity	NPD7115	Discovery
0.6154	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD7341	Phase 2
0.6132	Remote Similarity	NPD5167	Approved
0.6111	Remote Similarity	NPD6335	Approved
0.6098	Remote Similarity	NPD5777	Approved
0.6098	Remote Similarity	NPD4758	Discontinued

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