NPASS Compound

Structure

NPC1319 OpenBabel07101718312D 32 35 0 0 1 0 0 0 0 0999 V2000 3.1653 -5.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8126 -4.7859 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5909 -3.0032 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9641 2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 -1.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5472 -3.4190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5254 -3.6270 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2382 -2.4680 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 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 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 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 0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8344 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2601 -2.2601 0.0000 C 0 0 2 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 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 1 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 -4.3301 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 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 0.0000 -1.0000 0.0000 C 0 0 2 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 2.5388 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 2 19 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 11 1 0 0 0 0 10 19 2 0 0 0 0 11 20 1 0 0 0 0 12 13 1 0 0 0 0 12 22 2 0 0 0 0 13 24 1 0 0 0 0 14 17 1 0 0 0 0 14 21 1 0 0 0 0 15 16 1 0 0 0 0 15 25 1 0 0 0 0 16 28 1 0 0 0 0 17 29 1 0 0 0 0 18 23 1 0 0 0 0 18 30 1 0 0 0 0 20 3 1 1 0 0 0 20 26 1 0 0 0 0 21 22 1 0 0 0 0 21 28 1 6 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 6 0 0 0 24 27 1 0 0 0 0 24 28 1 6 0 0 0 25 27 1 0 0 0 0 25 32 1 6 0 0 0 26 29 1 1 0 0 0 28 6 1 6 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	442.38
Volume:	505.518
LogP:	7.678
LogD:	5.722
LogS:	-6.064
# Rotatable Bonds:	4
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.448
Synthetic Accessibility Score:	4.847
Fsp3:	0.867
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:	-4.816
MDCK Permeability:	1.20328504635836e-05
Pgp-inhibitor:	0.768
Pgp-substrate:	0.007
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	0.597

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.341
Plasma Protein Binding (PPB):	96.17859649658203%
Volume Distribution (VD):	1.185
Pgp-substrate:	2.51172137260437%

ADMET: Metabolism

CYP1A2-inhibitor:	0.041
CYP1A2-substrate:	0.183
CYP2C19-inhibitor:	0.141
CYP2C19-substrate:	0.925
CYP2C9-inhibitor:	0.287
CYP2C9-substrate:	0.167
CYP2D6-inhibitor:	0.02
CYP2D6-substrate:	0.053
CYP3A4-inhibitor:	0.904
CYP3A4-substrate:	0.643

ADMET: Excretion

Clearance (CL):	13.021
Half-life (T1/2):	0.026

ADMET: Toxicity

hERG Blockers:	0.266
Human Hepatotoxicity (H-HT):	0.485
Drug-inuced Liver Injury (DILI):	0.015
AMES Toxicity:	0.001
Rat Oral Acute Toxicity:	0.947
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.35
Carcinogencity:	0.052
Eye Corrosion:	0.041
Eye Irritation:	0.065
Respiratory Toxicity:	0.981

Download Data

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

Natural Product: NPC1319

Natural Product ID:	NPC1319
*Common Name:**	16-Hydroxybutyrospermol
IUPAC Name:	(3S,5R,9R,10R,13S,14S,16S,17S)-4,4,10,13,14-pentamethyl-17-[(2R)-6-methylhept-5-en-2-yl]-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
Synonyms:	16-Hydroxybutyrospermol
Standard InCHIKey:	MCOAOTHHQZUJEW-NHTPMSGWSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(2)10-9-11-20(3)26-23(31)18-30(8)22-12-13-24-27(4,5)25(32)15-16-28(24,6)21(22)14-17-29(26,30)7/h10,12,20-21,23-26,31-32H,9,11,13-18H2,1-8H3/t20-,21+,23+,24+,25+,26-,28-,29+,30-/m1/s1
SMILES:	CC(=CCC[C@@H](C)[C@@H]1[C@H](C[C@]2(C)C3=CC[C@H]4C(C)(C)[C@H](CC[C@]4(C)[C@H]3CC[C@@]12C)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL464492
PubChem CID:	44567125
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
NPO18596	Melia dubia	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12502333]
NPO18596	Melia dubia	Species	Meliaceae	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	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	=	2.5	ug ml-1	PMID[482522]

☑ 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 NPC1319 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	153
0.1-0.2	1417
0.2-0.3	7514
0.3-0.4	15933
0.4-0.5	6632
0.5-0.6	5270
0.6-0.7	3968
0.7-0.8	1336
0.8-0.85	286
0.85-0.9	126
0.9-0.95	58
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9595	High Similarity	NPC477522
0.9589	High Similarity	NPC189883
0.9459	High Similarity	NPC214570
0.9452	High Similarity	NPC471723
0.9452	High Similarity	NPC257347
0.9452	High Similarity	NPC141071
0.9359	High Similarity	NPC124172
0.9359	High Similarity	NPC209802
0.9351	High Similarity	NPC20853
0.9351	High Similarity	NPC201852
0.9342	High Similarity	NPC26117
0.9342	High Similarity	NPC236112
0.9333	High Similarity	NPC138621
0.9333	High Similarity	NPC244385
0.9333	High Similarity	NPC275910
0.9333	High Similarity	NPC6978
0.9333	High Similarity	NPC167037
0.9333	High Similarity	NPC285761
0.9333	High Similarity	NPC477514
0.9324	High Similarity	NPC96319
0.9324	High Similarity	NPC73875
0.9324	High Similarity	NPC134330
0.9324	High Similarity	NPC237460
0.9324	High Similarity	NPC46160
0.9324	High Similarity	NPC300324
0.9324	High Similarity	NPC107059
0.9324	High Similarity	NPC129165
0.9324	High Similarity	NPC240604
0.9324	High Similarity	NPC321381
0.9324	High Similarity	NPC321016
0.9324	High Similarity	NPC202642
0.9241	High Similarity	NPC318390
0.9231	High Similarity	NPC477818
0.9231	High Similarity	NPC110778
0.9221	High Similarity	NPC474531
0.9211	High Similarity	NPC30986
0.9211	High Similarity	NPC209430
0.9211	High Similarity	NPC80530
0.9211	High Similarity	NPC273410
0.92	High Similarity	NPC155986
0.92	High Similarity	NPC318495
0.92	High Similarity	NPC198968
0.9189	High Similarity	NPC22105
0.9189	High Similarity	NPC288035
0.9189	High Similarity	NPC322353
0.9189	High Similarity	NPC28657
0.9189	High Similarity	NPC134847
0.9189	High Similarity	NPC136188
0.9189	High Similarity	NPC304309
0.9189	High Similarity	NPC285893
0.9189	High Similarity	NPC118508
0.9189	High Similarity	NPC162742
0.9189	High Similarity	NPC230301
0.9189	High Similarity	NPC121744
0.9125	High Similarity	NPC24277
0.9103	High Similarity	NPC470049
0.9103	High Similarity	NPC470614
0.9103	High Similarity	NPC1272
0.9103	High Similarity	NPC30166
0.9091	High Similarity	NPC102253
0.9091	High Similarity	NPC322313
0.9091	High Similarity	NPC236237
0.9091	High Similarity	NPC13554
0.9079	High Similarity	NPC87604
0.9079	High Similarity	NPC205455
0.9079	High Similarity	NPC474216
0.9079	High Similarity	NPC85346
0.9079	High Similarity	NPC186191
0.9079	High Similarity	NPC65897
0.9079	High Similarity	NPC302041
0.9079	High Similarity	NPC473943
0.9067	High Similarity	NPC113733
0.9067	High Similarity	NPC470362
0.8987	High Similarity	NPC141941
0.8987	High Similarity	NPC193870
0.8974	High Similarity	NPC470383
0.8961	High Similarity	NPC28862
0.8961	High Similarity	NPC47982
0.8961	High Similarity	NPC143182
0.8961	High Similarity	NPC328714
0.8961	High Similarity	NPC84694
0.8961	High Similarity	NPC109546
0.8961	High Similarity	NPC81306
0.8947	High Similarity	NPC34019
0.8919	High Similarity	NPC474140
0.8919	High Similarity	NPC201373
0.8919	High Similarity	NPC182717
0.8902	High Similarity	NPC470542
0.8889	High Similarity	NPC201273
0.8875	High Similarity	NPC470077
0.8875	High Similarity	NPC127606
0.8875	High Similarity	NPC478102
0.8875	High Similarity	NPC475798
0.8861	High Similarity	NPC202389
0.8861	High Similarity	NPC87489
0.8861	High Similarity	NPC248886
0.8861	High Similarity	NPC296701
0.8861	High Similarity	NPC101462
0.8861	High Similarity	NPC49964
0.8861	High Similarity	NPC218616
0.8846	High Similarity	NPC234193
0.8846	High Similarity	NPC164840
0.8846	High Similarity	NPC209944
0.8846	High Similarity	NPC241290
0.8831	High Similarity	NPC312328
0.8831	High Similarity	NPC307965
0.8831	High Similarity	NPC76931
0.8831	High Similarity	NPC318136
0.8831	High Similarity	NPC18603
0.8831	High Similarity	NPC477819
0.8831	High Similarity	NPC42853
0.8831	High Similarity	NPC477817
0.8816	High Similarity	NPC247325
0.8816	High Similarity	NPC244488
0.88	High Similarity	NPC91858
0.88	High Similarity	NPC100334
0.88	High Similarity	NPC243342
0.88	High Similarity	NPC469593
0.88	High Similarity	NPC477138
0.88	High Similarity	NPC469534
0.88	High Similarity	NPC469533
0.8795	High Similarity	NPC105495
0.8784	High Similarity	NPC167706
0.8784	High Similarity	NPC111234
0.8765	High Similarity	NPC474189
0.8765	High Similarity	NPC474349
0.875	High Similarity	NPC113978
0.875	High Similarity	NPC317458
0.875	High Similarity	NPC207013
0.8734	High Similarity	NPC474683
0.8734	High Similarity	NPC47761
0.8734	High Similarity	NPC474731
0.8734	High Similarity	NPC264245
0.8734	High Similarity	NPC23852
0.8734	High Similarity	NPC474759
0.8734	High Similarity	NPC474752
0.8734	High Similarity	NPC209620
0.8734	High Similarity	NPC7505
0.8734	High Similarity	NPC82986
0.8734	High Similarity	NPC6707
0.8718	High Similarity	NPC49627
0.8718	High Similarity	NPC472463
0.8718	High Similarity	NPC49599
0.8701	High Similarity	NPC138502
0.8701	High Similarity	NPC90979
0.8701	High Similarity	NPC40394
0.8701	High Similarity	NPC260301
0.8701	High Similarity	NPC34177
0.8701	High Similarity	NPC307336
0.8701	High Similarity	NPC157996
0.8701	High Similarity	NPC471798
0.8701	High Similarity	NPC472805
0.8701	High Similarity	NPC101475
0.8684	High Similarity	NPC477923
0.8684	High Similarity	NPC66566
0.8684	High Similarity	NPC104387
0.8684	High Similarity	NPC240235
0.8684	High Similarity	NPC185536
0.8684	High Similarity	NPC230704
0.8684	High Similarity	NPC178383
0.8684	High Similarity	NPC291503
0.8684	High Similarity	NPC212879
0.8684	High Similarity	NPC231256
0.8684	High Similarity	NPC3403
0.8684	High Similarity	NPC70982
0.8675	High Similarity	NPC471952
0.8667	High Similarity	NPC471799
0.8659	High Similarity	NPC293287
0.8659	High Similarity	NPC152808
0.8659	High Similarity	NPC474970
0.8659	High Similarity	NPC94462
0.8659	High Similarity	NPC6605
0.8659	High Similarity	NPC125399
0.8659	High Similarity	NPC6391
0.8659	High Similarity	NPC261266
0.8659	High Similarity	NPC139724
0.8649	High Similarity	NPC45296
0.8642	High Similarity	NPC231310
0.8642	High Similarity	NPC185568
0.8642	High Similarity	NPC205845
0.8642	High Similarity	NPC82902
0.8642	High Similarity	NPC474047
0.863	High Similarity	NPC160209
0.8625	High Similarity	NPC50964
0.8625	High Similarity	NPC189972
0.8625	High Similarity	NPC5985
0.8608	High Similarity	NPC71535
0.8608	High Similarity	NPC78545
0.859	High Similarity	NPC300499
0.859	High Similarity	NPC472499
0.859	High Similarity	NPC472501
0.859	High Similarity	NPC472500
0.859	High Similarity	NPC253807
0.859	High Similarity	NPC98386
0.859	High Similarity	NPC470396
0.859	High Similarity	NPC158662
0.859	High Similarity	NPC99168
0.859	High Similarity	NPC230295
0.859	High Similarity	NPC196753
0.859	High Similarity	NPC22955

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 NPC1319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	151
0.1-0.2	1679
0.2-0.3	4554
0.3-0.4	1961
0.4-0.5	381
0.5-0.6	139
0.6-0.7	126
0.7-0.8	129
0.8-0.85	23
0.85-0.9	4
0.9-0.95	3
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9324	High Similarity	NPD3701	Clinical (unspecified phase)
0.9189	High Similarity	NPD7339	Approved
0.9189	High Similarity	NPD6942	Approved
0.9091	High Similarity	NPD7525	Registered
0.8784	High Similarity	NPD4243	Approved
0.8553	High Similarity	NPD4785	Approved
0.8553	High Similarity	NPD4784	Approved
0.8481	Intermediate Similarity	NPD7645	Phase 2
0.8415	Intermediate Similarity	NPD4786	Approved
0.8375	Intermediate Similarity	NPD4748	Discontinued
0.8353	Intermediate Similarity	NPD5328	Approved
0.8333	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8312	Intermediate Similarity	NPD6926	Approved
0.8312	Intermediate Similarity	NPD6924	Approved
0.8276	Intermediate Similarity	NPD4202	Approved
0.8214	Intermediate Similarity	NPD3618	Phase 1
0.8205	Intermediate Similarity	NPD5275	Approved
0.8205	Intermediate Similarity	NPD4190	Phase 3
0.8193	Intermediate Similarity	NPD3665	Phase 1
0.8193	Intermediate Similarity	NPD3666	Approved
0.8193	Intermediate Similarity	NPD3133	Approved
0.8171	Intermediate Similarity	NPD3667	Approved
0.8161	Intermediate Similarity	NPD6079	Approved
0.8101	Intermediate Similarity	NPD6933	Approved
0.8052	Intermediate Similarity	NPD7151	Approved
0.8052	Intermediate Similarity	NPD7152	Approved
0.8052	Intermediate Similarity	NPD7150	Approved
0.8026	Intermediate Similarity	NPD6923	Approved
0.8026	Intermediate Similarity	NPD6922	Approved
0.8025	Intermediate Similarity	NPD4195	Approved
0.7922	Intermediate Similarity	NPD7143	Approved
0.7922	Intermediate Similarity	NPD7144	Approved
0.7912	Intermediate Similarity	NPD4755	Approved
0.7805	Intermediate Similarity	NPD6929	Approved
0.7742	Intermediate Similarity	NPD5286	Approved
0.7742	Intermediate Similarity	NPD4700	Approved
0.7742	Intermediate Similarity	NPD4696	Approved
0.7742	Intermediate Similarity	NPD5285	Approved
0.7738	Intermediate Similarity	NPD4223	Phase 3
0.7738	Intermediate Similarity	NPD4221	Approved
0.7727	Intermediate Similarity	NPD4753	Phase 2
0.7711	Intermediate Similarity	NPD7509	Discontinued
0.7711	Intermediate Similarity	NPD6931	Approved
0.7711	Intermediate Similarity	NPD6930	Phase 2
0.7674	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD5329	Approved
0.766	Intermediate Similarity	NPD5223	Approved
0.7609	Intermediate Similarity	NPD4697	Phase 3
0.7609	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7609	Intermediate Similarity	NPD5222	Approved
0.7609	Intermediate Similarity	NPD5221	Approved
0.7579	Intermediate Similarity	NPD5225	Approved
0.7579	Intermediate Similarity	NPD5226	Approved
0.7579	Intermediate Similarity	NPD4633	Approved
0.7579	Intermediate Similarity	NPD5224	Approved
0.7579	Intermediate Similarity	NPD5211	Phase 2
0.7561	Intermediate Similarity	NPD5776	Phase 2
0.7561	Intermediate Similarity	NPD6932	Approved
0.7561	Intermediate Similarity	NPD6925	Approved
0.7558	Intermediate Similarity	NPD4197	Approved
0.7527	Intermediate Similarity	NPD5173	Approved
0.7526	Intermediate Similarity	NPD7128	Approved
0.7526	Intermediate Similarity	NPD6402	Approved
0.7526	Intermediate Similarity	NPD5739	Approved
0.7526	Intermediate Similarity	NPD6675	Approved
0.75	Intermediate Similarity	NPD5175	Approved
0.75	Intermediate Similarity	NPD5174	Approved
0.75	Intermediate Similarity	NPD4754	Approved
0.7473	Intermediate Similarity	NPD6399	Phase 3
0.747	Intermediate Similarity	NPD7145	Approved
0.7468	Intermediate Similarity	NPD4787	Phase 1
0.7447	Intermediate Similarity	NPD7638	Approved
0.7442	Intermediate Similarity	NPD4788	Approved
0.7442	Intermediate Similarity	NPD6695	Phase 3
0.7423	Intermediate Similarity	NPD5141	Approved
0.7386	Intermediate Similarity	NPD5279	Phase 3
0.7386	Intermediate Similarity	NPD4688	Approved
0.7386	Intermediate Similarity	NPD4690	Approved
0.7386	Intermediate Similarity	NPD4138	Approved
0.7386	Intermediate Similarity	NPD4689	Approved
0.7386	Intermediate Similarity	NPD4693	Phase 3
0.7386	Intermediate Similarity	NPD6409	Approved
0.7386	Intermediate Similarity	NPD6684	Approved
0.7386	Intermediate Similarity	NPD5205	Approved
0.7386	Intermediate Similarity	NPD7334	Approved
0.7386	Intermediate Similarity	NPD7521	Approved
0.7386	Intermediate Similarity	NPD7146	Approved
0.7386	Intermediate Similarity	NPD5330	Approved
0.7381	Intermediate Similarity	NPD6683	Phase 2
0.7374	Intermediate Similarity	NPD6881	Approved
0.7374	Intermediate Similarity	NPD7320	Approved
0.7374	Intermediate Similarity	NPD6899	Approved
0.7368	Intermediate Similarity	NPD7640	Approved
0.7368	Intermediate Similarity	NPD7639	Approved
0.7363	Intermediate Similarity	NPD7515	Phase 2
0.7356	Intermediate Similarity	NPD3668	Phase 3
0.7356	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4768	Approved
0.7347	Intermediate Similarity	NPD4767	Approved
0.7342	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD6084	Phase 2
0.734	Intermediate Similarity	NPD6083	Phase 2
0.7333	Intermediate Similarity	NPD6051	Approved
0.7317	Intermediate Similarity	NPD8264	Approved
0.7312	Intermediate Similarity	NPD4629	Approved
0.7312	Intermediate Similarity	NPD5210	Approved
0.73	Intermediate Similarity	NPD6373	Approved
0.73	Intermediate Similarity	NPD6372	Approved
0.7294	Intermediate Similarity	NPD7514	Phase 3
0.7273	Intermediate Similarity	NPD6893	Approved
0.7273	Intermediate Similarity	NPD5701	Approved
0.7273	Intermediate Similarity	NPD5697	Approved
0.7263	Intermediate Similarity	NPD5290	Discontinued
0.7262	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD6883	Approved
0.7228	Intermediate Similarity	NPD7102	Approved
0.7228	Intermediate Similarity	NPD7290	Approved
0.7222	Intermediate Similarity	NPD4722	Approved
0.7222	Intermediate Similarity	NPD4723	Approved
0.7222	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7222	Intermediate Similarity	NPD6903	Approved
0.7209	Intermediate Similarity	NPD6902	Approved
0.72	Intermediate Similarity	NPD6011	Approved
0.72	Intermediate Similarity	NPD4730	Approved
0.72	Intermediate Similarity	NPD5128	Approved
0.72	Intermediate Similarity	NPD4729	Approved
0.7191	Intermediate Similarity	NPD5690	Phase 2
0.7191	Intermediate Similarity	NPD4694	Approved
0.7191	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5280	Approved
0.7157	Intermediate Similarity	NPD8130	Phase 1
0.7157	Intermediate Similarity	NPD6650	Approved
0.7157	Intermediate Similarity	NPD6617	Approved
0.7157	Intermediate Similarity	NPD6869	Approved
0.7157	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7157	Intermediate Similarity	NPD6649	Approved
0.7157	Intermediate Similarity	NPD6847	Approved
0.7129	Intermediate Similarity	NPD6014	Approved
0.7129	Intermediate Similarity	NPD6012	Approved
0.7129	Intermediate Similarity	NPD6013	Approved
0.7111	Intermediate Similarity	NPD7750	Discontinued
0.7111	Intermediate Similarity	NPD7524	Approved
0.7093	Intermediate Similarity	NPD7332	Phase 2
0.7087	Intermediate Similarity	NPD8297	Approved
0.7087	Intermediate Similarity	NPD6882	Approved
0.7059	Intermediate Similarity	NPD5249	Phase 3
0.7059	Intermediate Similarity	NPD5248	Approved
0.7059	Intermediate Similarity	NPD5250	Approved
0.7059	Intermediate Similarity	NPD5169	Approved
0.7059	Intermediate Similarity	NPD5251	Approved
0.7059	Intermediate Similarity	NPD5247	Approved
0.7059	Intermediate Similarity	NPD4634	Approved
0.7059	Intermediate Similarity	NPD5134	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD5135	Approved
0.7021	Intermediate Similarity	NPD7748	Approved
0.7011	Intermediate Similarity	NPD4692	Approved
0.7011	Intermediate Similarity	NPD6898	Phase 1
0.7011	Intermediate Similarity	NPD4139	Approved
0.7	Intermediate Similarity	NPD6098	Approved
0.699	Remote Similarity	NPD5216	Approved
0.699	Remote Similarity	NPD5217	Approved
0.699	Remote Similarity	NPD5215	Approved
0.699	Remote Similarity	NPD5127	Approved
0.6989	Remote Similarity	NPD8035	Phase 2
0.6989	Remote Similarity	NPD8034	Phase 2
0.6951	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6951	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6947	Remote Similarity	NPD5695	Phase 3
0.6939	Remote Similarity	NPD4159	Approved
0.6907	Remote Similarity	NPD5696	Approved
0.6863	Remote Similarity	NPD5168	Approved
0.686	Remote Similarity	NPD3617	Approved
0.6857	Remote Similarity	NPD4632	Approved
0.6848	Remote Similarity	NPD6672	Approved
0.6848	Remote Similarity	NPD5737	Approved
0.6829	Remote Similarity	NPD4245	Approved
0.6829	Remote Similarity	NPD4244	Approved
0.6824	Remote Similarity	NPD6117	Approved
0.6809	Remote Similarity	NPD5284	Approved
0.6809	Remote Similarity	NPD7087	Discontinued
0.6809	Remote Similarity	NPD5281	Approved
0.6804	Remote Similarity	NPD7902	Approved
0.6792	Remote Similarity	NPD5167	Approved
0.6786	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6080	Approved
0.6774	Remote Similarity	NPD6904	Approved
0.6774	Remote Similarity	NPD6673	Approved
0.6765	Remote Similarity	NPD6412	Phase 2
0.6759	Remote Similarity	NPD6335	Approved
0.6744	Remote Similarity	NPD6116	Phase 1
0.6729	Remote Similarity	NPD6274	Approved
0.6707	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD3698	Phase 2
0.6705	Remote Similarity	NPD6928	Phase 2
0.6702	Remote Similarity	NPD4096	Approved
0.67	Remote Similarity	NPD7632	Discontinued
0.6697	Remote Similarity	NPD7100	Approved
0.6697	Remote Similarity	NPD7101	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