NPASS Compound

Structure

NPC137461 OpenBabel07101719142D 32 36 0 0 1 0 0 0 0 0999 V2000 -2.8289 7.1974 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1161 8.3564 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7633 7.8212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1890 5.5032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1913 4.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4980 6.4543 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8363 4.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1453 5.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1369 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5491 2.1910 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7852 7.6132 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8581 4.7601 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4762 6.6622 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.5491 3.8090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 2.5000 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 -1.7321 1.0000 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 -2.5981 3.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 17 1 0 0 0 0 3 17 1 0 0 0 0 6 28 1 0 0 0 0 8 9 1 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 21 1 0 0 0 0 11 22 1 0 0 0 0 12 15 1 0 0 0 0 12 20 1 0 0 0 0 13 14 1 0 0 0 0 13 23 1 0 0 0 0 14 27 1 0 0 0 0 15 28 1 0 0 0 0 16 20 1 0 0 0 0 17 19 1 0 0 0 0 18 4 1 1 0 0 0 18 21 1 0 0 0 0 19 7 1 6 0 0 0 20 30 1 6 0 0 0 21 27 1 6 0 0 0 22 24 1 0 0 0 0 22 27 1 6 0 0 0 23 24 2 0 0 0 0 23 28 1 0 0 0 0 24 25 1 0 0 0 0 25 26 1 0 0 0 0 25 31 1 1 0 0 0 26 29 1 6 0 0 0 26 32 1 0 0 0 0 27 5 1 6 0 0 0 28 29 1 6 0 0 0 29 16 1 6 0 0 0 29 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	444.36
Volume:	491.092
LogP:	5.784
LogD:	5.438
LogS:	-5.195
# Rotatable Bonds:	6
TPSA:	52.99
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	5
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.375
Synthetic Accessibility Score:	5.572
Fsp3:	0.931
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:	-4.891
MDCK Permeability:	3.5669232602231205e-05
Pgp-inhibitor:	0.216
Pgp-substrate:	0.171
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.711
30% Bioavailability (F30%):	0.728

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.026
Plasma Protein Binding (PPB):	93.91980743408203%
Volume Distribution (VD):	1.292
Pgp-substrate:	1.5313663482666016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.562
CYP2C19-inhibitor:	0.132
CYP2C19-substrate:	0.949
CYP2C9-inhibitor:	0.293
CYP2C9-substrate:	0.085
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.246
CYP3A4-inhibitor:	0.738
CYP3A4-substrate:	0.793

ADMET: Excretion

Clearance (CL):	7.58
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.069
Human Hepatotoxicity (H-HT):	0.147
Drug-inuced Liver Injury (DILI):	0.083
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.037
Maximum Recommended Daily Dose:	0.243
Skin Sensitization:	0.082
Carcinogencity:	0.01
Eye Corrosion:	0.034
Eye Irritation:	0.434
Respiratory Toxicity:	0.933

Download Data

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

Natural Product: NPC137461

Natural Product ID:	NPC137461
*Common Name:**	GMXNULASJRVJLO-SFYMJXGPSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	GMXNULASJRVJLO-SFYMJXGPSA-N
Standard InCHI:	InChI=1S/C29H48O3/c1-7-19(17(2)3)9-8-18(4)21-10-11-22-24-23(13-14-27(21,22)5)28(6)15-12-20(30)16-29(28)26(32-29)25(24)31/h17-22,25-26,30-31H,7-16H2,1-6H3/t18-,19-,20+,21-,22+,25+,26+,27-,28-,29+/m1/s1
SMILES:	CC[C@H](CC[C@@H](C)[C@H]1CC[C@H]2C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C[C@@]21[C@H]([C@H]3O)O2)O)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL482801
PubChem CID:	11080765
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
NPO16948	Polymastia tenax	Species	Polymastiidae	Eukaryota	n.a.	Colombian	n.a.	PMID[12193022]
NPO16948	Polymastia tenax	Species	Polymastiidae	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
Others	5

Activity Type	# Activity
Cell Line	3
NON-MOLECULAR	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	LC50	=	1.0	ug.mL-1	PMID[557389]
NPT139	Cell Line	HT-29	Homo sapiens	LC50	=	1.0	ug.mL-1	PMID[557389]
NPT306	Cell Line	PC-3	Homo sapiens	LC50	=	1.0	ug.mL-1	PMID[557389]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	LC50	=	1.0	ug.mL-1	PMID[557389]
NPT27	Others	Unspecified		LC50	=	0.5	ug.mL-1	PMID[557389]

☑ 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 NPC137461 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	1857
0.2-0.3	5777
0.3-0.4	14096
0.4-0.5	9396
0.5-0.6	6895
0.6-0.7	3941
0.7-0.8	492
0.8-0.85	26
0.85-0.9	2
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9556	High Similarity	NPC261807
0.9432	High Similarity	NPC114389
0.9022	High Similarity	NPC103165
0.9022	High Similarity	NPC210717
0.8817	High Similarity	NPC72204
0.8778	High Similarity	NPC470361
0.871	High Similarity	NPC8774
0.8696	High Similarity	NPC310013
0.8681	High Similarity	NPC3345
0.8681	High Similarity	NPC291484
0.8681	High Similarity	NPC80561
0.8681	High Similarity	NPC204188
0.8681	High Similarity	NPC11216
0.8681	High Similarity	NPC329596
0.8617	High Similarity	NPC227583
0.8617	High Similarity	NPC98457
0.8617	High Similarity	NPC288970
0.8617	High Similarity	NPC12103
0.8602	High Similarity	NPC65402
0.8602	High Similarity	NPC127718
0.8587	High Similarity	NPC41554
0.8587	High Similarity	NPC97404
0.8523	High Similarity	NPC132635
0.8495	Intermediate Similarity	NPC119379
0.8454	Intermediate Similarity	NPC476896
0.8444	Intermediate Similarity	NPC125399
0.8409	Intermediate Similarity	NPC7988
0.8387	Intermediate Similarity	NPC210268
0.828	Intermediate Similarity	NPC192437
0.828	Intermediate Similarity	NPC270511
0.828	Intermediate Similarity	NPC245410
0.828	Intermediate Similarity	NPC470390
0.8261	Intermediate Similarity	NPC280556
0.8261	Intermediate Similarity	NPC474668
0.8261	Intermediate Similarity	NPC133588
0.8247	Intermediate Similarity	NPC275865
0.8247	Intermediate Similarity	NPC476895
0.8242	Intermediate Similarity	NPC6391
0.8242	Intermediate Similarity	NPC255143
0.8242	Intermediate Similarity	NPC299068
0.8222	Intermediate Similarity	NPC86238
0.8222	Intermediate Similarity	NPC474047
0.8211	Intermediate Similarity	NPC144202
0.8182	Intermediate Similarity	NPC22403
0.8152	Intermediate Similarity	NPC233744
0.8144	Intermediate Similarity	NPC476893
0.8144	Intermediate Similarity	NPC476021
0.8144	Intermediate Similarity	NPC474994
0.8144	Intermediate Similarity	NPC476040
0.8132	Intermediate Similarity	NPC470360
0.8111	Intermediate Similarity	NPC475789
0.8105	Intermediate Similarity	NPC27531
0.8105	Intermediate Similarity	NPC27918
0.8085	Intermediate Similarity	NPC14380
0.8085	Intermediate Similarity	NPC295668
0.8081	Intermediate Similarity	NPC475617
0.8065	Intermediate Similarity	NPC67872
0.8065	Intermediate Similarity	NPC473436
0.8043	Intermediate Similarity	NPC94462
0.8043	Intermediate Similarity	NPC261266
0.8022	Intermediate Similarity	NPC185568
0.8021	Intermediate Similarity	NPC474922
0.802	Intermediate Similarity	NPC473543
0.802	Intermediate Similarity	NPC75608
0.8	Intermediate Similarity	NPC87489
0.8	Intermediate Similarity	NPC275671
0.798	Intermediate Similarity	NPC79303
0.798	Intermediate Similarity	NPC324598
0.7979	Intermediate Similarity	NPC138974
0.7979	Intermediate Similarity	NPC115607
0.7978	Intermediate Similarity	NPC16449
0.7961	Intermediate Similarity	NPC472218
0.7961	Intermediate Similarity	NPC472219
0.7961	Intermediate Similarity	NPC472217
0.7941	Intermediate Similarity	NPC472898
0.7941	Intermediate Similarity	NPC472899
0.7941	Intermediate Similarity	NPC472900
0.7938	Intermediate Similarity	NPC476894
0.7938	Intermediate Similarity	NPC86893
0.7938	Intermediate Similarity	NPC292178
0.7935	Intermediate Similarity	NPC474349
0.7935	Intermediate Similarity	NPC474189
0.7921	Intermediate Similarity	NPC474124
0.7921	Intermediate Similarity	NPC473523
0.7917	Intermediate Similarity	NPC307776
0.7917	Intermediate Similarity	NPC98193
0.7912	Intermediate Similarity	NPC317458
0.7912	Intermediate Similarity	NPC474634
0.7912	Intermediate Similarity	NPC477978
0.79	Intermediate Similarity	NPC476897
0.79	Intermediate Similarity	NPC470434
0.7895	Intermediate Similarity	NPC473269
0.7895	Intermediate Similarity	NPC191323
0.7889	Intermediate Similarity	NPC470383
0.7889	Intermediate Similarity	NPC23852
0.7889	Intermediate Similarity	NPC6707
0.7889	Intermediate Similarity	NPC209620
0.7885	Intermediate Similarity	NPC472901
0.7879	Intermediate Similarity	NPC5358
0.7879	Intermediate Similarity	NPC216260
0.7857	Intermediate Similarity	NPC276103
0.7857	Intermediate Similarity	NPC129569
0.7857	Intermediate Similarity	NPC54248
0.7849	Intermediate Similarity	NPC293287
0.7849	Intermediate Similarity	NPC71520
0.7849	Intermediate Similarity	NPC269058
0.7849	Intermediate Similarity	NPC152808
0.7849	Intermediate Similarity	NPC476217
0.7843	Intermediate Similarity	NPC471111
0.7835	Intermediate Similarity	NPC473258
0.7835	Intermediate Similarity	NPC477605
0.783	Intermediate Similarity	NPC477050
0.7826	Intermediate Similarity	NPC15534
0.7826	Intermediate Similarity	NPC83702
0.7826	Intermediate Similarity	NPC205845
0.7826	Intermediate Similarity	NPC231310
0.7826	Intermediate Similarity	NPC238485
0.7822	Intermediate Similarity	NPC22634
0.7822	Intermediate Similarity	NPC475344
0.7822	Intermediate Similarity	NPC476471
0.7812	Intermediate Similarity	NPC471453
0.7802	Intermediate Similarity	NPC30166
0.7802	Intermediate Similarity	NPC101462
0.7802	Intermediate Similarity	NPC49964
0.7802	Intermediate Similarity	NPC202389
0.7802	Intermediate Similarity	NPC471408
0.7802	Intermediate Similarity	NPC50964
0.78	Intermediate Similarity	NPC469942
0.78	Intermediate Similarity	NPC188968
0.78	Intermediate Similarity	NPC271295
0.78	Intermediate Similarity	NPC471242
0.78	Intermediate Similarity	NPC473510
0.7791	Intermediate Similarity	NPC201373
0.7789	Intermediate Similarity	NPC97103
0.7789	Intermediate Similarity	NPC49783
0.7789	Intermediate Similarity	NPC101886
0.7778	Intermediate Similarity	NPC475032
0.7778	Intermediate Similarity	NPC475033
0.7778	Intermediate Similarity	NPC254121
0.7778	Intermediate Similarity	NPC473244
0.7778	Intermediate Similarity	NPC210337
0.7767	Intermediate Similarity	NPC474015
0.7766	Intermediate Similarity	NPC304083
0.7766	Intermediate Similarity	NPC149224
0.7766	Intermediate Similarity	NPC476948
0.7766	Intermediate Similarity	NPC189777
0.7766	Intermediate Similarity	NPC470620
0.7757	Intermediate Similarity	NPC317210
0.7753	Intermediate Similarity	NPC275910
0.7745	Intermediate Similarity	NPC475701
0.7745	Intermediate Similarity	NPC55954
0.7745	Intermediate Similarity	NPC473198
0.7745	Intermediate Similarity	NPC218513
0.7742	Intermediate Similarity	NPC16350
0.7742	Intermediate Similarity	NPC290731
0.7742	Intermediate Similarity	NPC266511
0.7742	Intermediate Similarity	NPC274448
0.7742	Intermediate Similarity	NPC308041
0.7736	Intermediate Similarity	NPC472987
0.7736	Intermediate Similarity	NPC473021
0.7727	Intermediate Similarity	NPC73875
0.7717	Intermediate Similarity	NPC216420
0.7717	Intermediate Similarity	NPC85095
0.7717	Intermediate Similarity	NPC113978
0.7717	Intermediate Similarity	NPC211135
0.7717	Intermediate Similarity	NPC470384
0.7714	Intermediate Similarity	NPC284828
0.7714	Intermediate Similarity	NPC5475
0.7714	Intermediate Similarity	NPC173905
0.7714	Intermediate Similarity	NPC472216
0.7714	Intermediate Similarity	NPC128133
0.7708	Intermediate Similarity	NPC473956
0.7708	Intermediate Similarity	NPC475751
0.7708	Intermediate Similarity	NPC10274
0.77	Intermediate Similarity	NPC470068
0.77	Intermediate Similarity	NPC102426
0.77	Intermediate Similarity	NPC470067
0.77	Intermediate Similarity	NPC470066
0.77	Intermediate Similarity	NPC300179
0.7692	Intermediate Similarity	NPC476646
0.7692	Intermediate Similarity	NPC264245
0.7692	Intermediate Similarity	NPC70927
0.7692	Intermediate Similarity	NPC249423
0.7692	Intermediate Similarity	NPC33053
0.7692	Intermediate Similarity	NPC474531
0.7692	Intermediate Similarity	NPC231340
0.7692	Intermediate Similarity	NPC473165
0.7684	Intermediate Similarity	NPC4574
0.7684	Intermediate Similarity	NPC471952
0.7684	Intermediate Similarity	NPC475605
0.7684	Intermediate Similarity	NPC212596
0.7677	Intermediate Similarity	NPC221801
0.7677	Intermediate Similarity	NPC90583
0.7677	Intermediate Similarity	NPC471903
0.7677	Intermediate Similarity	NPC284194
0.7677	Intermediate Similarity	NPC211810
0.7677	Intermediate Similarity	NPC471765
0.7677	Intermediate Similarity	NPC88009
0.767	Intermediate Similarity	NPC152966
0.767	Intermediate Similarity	NPC187400

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 NPC137461 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	2298
0.2-0.3	4105
0.3-0.4	1753
0.4-0.5	453
0.5-0.6	254
0.6-0.7	80
0.7-0.8	11
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
0.7766	Intermediate Similarity	NPD7524	Approved
0.7723	Intermediate Similarity	NPD4159	Approved
0.7634	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD6695	Phase 3
0.7396	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD7525	Registered
0.7391	Intermediate Similarity	NPD4748	Discontinued
0.7391	Intermediate Similarity	NPD6930	Phase 2
0.7391	Intermediate Similarity	NPD6931	Approved
0.7383	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6929	Approved
0.7222	Intermediate Similarity	NPD6942	Approved
0.7222	Intermediate Similarity	NPD7339	Approved
0.7216	Intermediate Similarity	NPD7750	Discontinued
0.7204	Intermediate Similarity	NPD7514	Phase 3
0.7128	Intermediate Similarity	NPD6902	Approved
0.708	Intermediate Similarity	NPD7115	Discovery
0.7065	Intermediate Similarity	NPD5776	Phase 2
0.7065	Intermediate Similarity	NPD6925	Approved
0.7048	Intermediate Similarity	NPD5344	Discontinued
0.7021	Intermediate Similarity	NPD7332	Phase 2
0.7018	Intermediate Similarity	NPD7328	Approved
0.7018	Intermediate Similarity	NPD7327	Approved
0.701	Intermediate Similarity	NPD6893	Approved
0.7	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD7145	Approved
0.6957	Remote Similarity	NPD6933	Approved
0.6957	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD7516	Approved
0.6952	Remote Similarity	NPD7639	Approved
0.6952	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7087	Discontinued
0.6915	Remote Similarity	NPD7645	Phase 2
0.6882	Remote Similarity	NPD6932	Approved
0.6857	Remote Similarity	NPD7638	Approved
0.6854	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6838	Remote Similarity	NPD8380	Approved
0.6838	Remote Similarity	NPD8296	Approved
0.6838	Remote Similarity	NPD8335	Approved
0.6838	Remote Similarity	NPD8033	Approved
0.6838	Remote Similarity	NPD8378	Approved
0.6838	Remote Similarity	NPD8379	Approved
0.6822	Remote Similarity	NPD7632	Discontinued
0.6771	Remote Similarity	NPD6898	Phase 1
0.6752	Remote Similarity	NPD8377	Approved
0.6752	Remote Similarity	NPD8294	Approved
0.6739	Remote Similarity	NPD6926	Approved
0.6739	Remote Similarity	NPD6924	Approved
0.6737	Remote Similarity	NPD6683	Phase 2
0.6735	Remote Similarity	NPD4786	Approved
0.6727	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6695	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8264	Approved
0.6636	Remote Similarity	NPD6648	Approved
0.6607	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD7637	Suspended
0.6577	Remote Similarity	NPD6412	Phase 2
0.6569	Remote Similarity	NPD5328	Approved
0.6559	Remote Similarity	NPD4785	Approved
0.6559	Remote Similarity	NPD4784	Approved
0.6542	Remote Similarity	NPD4225	Approved
0.6538	Remote Similarity	NPD6399	Phase 3
0.6538	Remote Similarity	NPD4202	Approved
0.6531	Remote Similarity	NPD3667	Approved
0.6522	Remote Similarity	NPD4632	Approved
0.6522	Remote Similarity	NPD4243	Approved
0.6514	Remote Similarity	NPD5211	Phase 2
0.6505	Remote Similarity	NPD3168	Discontinued
0.6495	Remote Similarity	NPD7509	Discontinued
0.6486	Remote Similarity	NPD6402	Approved
0.6486	Remote Similarity	NPD7128	Approved
0.6486	Remote Similarity	NPD6008	Approved
0.6486	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD6675	Approved
0.6477	Remote Similarity	NPD371	Approved
0.6475	Remote Similarity	NPD7507	Approved
0.6471	Remote Similarity	NPD6059	Approved
0.6471	Remote Similarity	NPD6319	Approved
0.6471	Remote Similarity	NPD6054	Approved
0.6458	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD7319	Approved
0.6449	Remote Similarity	NPD4755	Approved
0.6442	Remote Similarity	NPD6079	Approved
0.6436	Remote Similarity	NPD3618	Phase 1
0.6435	Remote Similarity	NPD8297	Approved
0.6404	Remote Similarity	NPD4634	Approved
0.6396	Remote Similarity	NPD5141	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD6899	Approved
0.6372	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD6370	Approved
0.6344	Remote Similarity	NPD7150	Approved
0.6344	Remote Similarity	NPD7152	Approved
0.6344	Remote Similarity	NPD7151	Approved
0.6339	Remote Similarity	NPD6640	Phase 3
0.633	Remote Similarity	NPD5286	Approved
0.633	Remote Similarity	NPD5285	Approved
0.633	Remote Similarity	NPD4696	Approved
0.633	Remote Similarity	NPD4700	Approved
0.6327	Remote Similarity	NPD6928	Phase 2
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6311	Remote Similarity	NPD7604	Phase 2
0.6304	Remote Similarity	NPD6923	Approved
0.6304	Remote Similarity	NPD6922	Approved
0.6283	Remote Similarity	NPD5697	Approved
0.6283	Remote Similarity	NPD5701	Approved
0.6281	Remote Similarity	NPD6015	Approved
0.6281	Remote Similarity	NPD6016	Approved
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD6883	Approved
0.6261	Remote Similarity	NPD7290	Approved
0.626	Remote Similarity	NPD7492	Approved
0.625	Remote Similarity	NPD6051	Approved
0.6239	Remote Similarity	NPD8133	Approved
0.6237	Remote Similarity	NPD7144	Approved
0.6237	Remote Similarity	NPD7143	Approved
0.623	Remote Similarity	NPD5988	Approved
0.6228	Remote Similarity	NPD6686	Approved
0.6228	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD8171	Discontinued
0.6218	Remote Similarity	NPD6009	Approved
0.6218	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5225	Approved
0.6216	Remote Similarity	NPD5226	Approved
0.6216	Remote Similarity	NPD5224	Approved
0.6216	Remote Similarity	NPD4633	Approved
0.621	Remote Similarity	NPD6616	Approved
0.6207	Remote Similarity	NPD6649	Approved
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD6617	Approved
0.6207	Remote Similarity	NPD6650	Approved
0.6176	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6012	Approved
0.6174	Remote Similarity	NPD6013	Approved
0.6174	Remote Similarity	NPD6014	Approved
0.6161	Remote Similarity	NPD5175	Approved
0.6161	Remote Similarity	NPD5174	Approved
0.616	Remote Similarity	NPD7078	Approved
0.616	Remote Similarity	NPD8293	Discontinued
0.6154	Remote Similarity	NPD6053	Discontinued
0.6154	Remote Similarity	NPD6882	Approved
0.6148	Remote Similarity	NPD5983	Phase 2
0.6147	Remote Similarity	NPD6084	Phase 2
0.6147	Remote Similarity	NPD6083	Phase 2
0.6146	Remote Similarity	NPD4190	Phase 3
0.6146	Remote Similarity	NPD5275	Approved
0.6132	Remote Similarity	NPD8035	Phase 2
0.6132	Remote Similarity	NPD8034	Phase 2
0.6126	Remote Similarity	NPD5223	Approved
0.6117	Remote Similarity	NPD5279	Phase 3
0.6111	Remote Similarity	NPD7736	Approved
0.6111	Remote Similarity	NPD5695	Phase 3
0.61	Remote Similarity	NPD4139	Approved
0.61	Remote Similarity	NPD4692	Approved
0.6095	Remote Similarity	NPD4753	Phase 2
0.6087	Remote Similarity	NPD6011	Approved
0.608	Remote Similarity	NPD6336	Discontinued
0.6078	Remote Similarity	NPD3665	Phase 1
0.6078	Remote Similarity	NPD3133	Approved
0.6078	Remote Similarity	NPD3666	Approved
0.6075	Remote Similarity	NPD5779	Approved
0.6075	Remote Similarity	NPD5778	Approved
0.6068	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6067	Remote Similarity	NPD368	Approved
0.6066	Remote Similarity	NPD7741	Discontinued
0.6064	Remote Similarity	NPD4787	Phase 1
0.6061	Remote Similarity	NPD4195	Approved
0.6055	Remote Similarity	NPD4697	Phase 3
0.6055	Remote Similarity	NPD5222	Approved
0.6055	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD5221	Approved
0.6053	Remote Similarity	NPD4768	Approved
0.6053	Remote Similarity	NPD4767	Approved
0.6053	Remote Similarity	NPD5357	Phase 1
0.6038	Remote Similarity	NPD7838	Discovery
0.6038	Remote Similarity	NPD46	Approved
0.6038	Remote Similarity	NPD7136	Phase 2
0.6038	Remote Similarity	NPD6698	Approved
0.6018	Remote Similarity	NPD4754	Approved
0.6	Remote Similarity	NPD5173	Approved
0.5984	Remote Similarity	NPD6033	Approved
0.5983	Remote Similarity	NPD6371	Approved
0.596	Remote Similarity	NPD6114	Approved
0.596	Remote Similarity	NPD6697	Approved
0.596	Remote Similarity	NPD6118	Approved
0.596	Remote Similarity	NPD6115	Approved
0.5948	Remote Similarity	NPD5128	Approved
0.5948	Remote Similarity	NPD4730	Approved
0.5948	Remote Similarity	NPD4729	Approved
0.5929	Remote Similarity	NPD3653	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD3668	Phase 3
0.592	Remote Similarity	NPD6067	Discontinued
0.5887	Remote Similarity	NPD8515	Approved
0.5887	Remote Similarity	NPD8517	Approved
0.5887	Remote Similarity	NPD8513	Phase 3
0.5887	Remote Similarity	NPD8516	Approved
0.5882	Remote Similarity	NPD4221	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