NPASS Compound

Structure

NPC474759 OpenBabel07101718232D 32 35 0 0 1 0 0 0 0 0999 V2000 -4.7515 -2.4328 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0387 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7004 -5.0780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4570 -3.5032 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 -0.4593 -2.4135 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 -2.4049 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8171 -0.1910 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 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4133 -3.9190 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 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 -5.0605 -3.3838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3914 -4.1270 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.1261 -2.7601 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 3.4641 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8171 -1.8090 0.0000 C 0 0 3 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 0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.1042 -2.9680 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7734 -2.2248 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 5 28 1 0 0 0 0 6 29 1 0 0 0 0 7 32 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 21 1 0 0 0 0 11 13 1 0 0 0 0 11 24 1 0 0 0 0 12 28 1 0 0 0 0 13 29 1 0 0 0 0 14 18 1 0 0 0 0 14 25 1 0 0 0 0 15 20 1 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 26 1 0 0 0 0 17 18 1 0 0 0 0 18 3 1 1 0 0 0 19 4 1 6 0 0 0 19 22 1 0 0 0 0 19 25 1 0 0 0 0 20 28 1 0 0 0 0 21 30 1 1 0 0 0 22 29 1 0 0 0 0 23 27 1 0 0 0 0 23 29 1 1 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 31 1 1 0 0 0 26 27 1 0 0 0 0 26 32 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	446.38
Volume:	499.648
LogP:	5.463
LogD:	4.969
LogS:	-5.684
# Rotatable Bonds:	6
TPSA:	49.69
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.475
Synthetic Accessibility Score:	4.866
Fsp3:	0.931
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.697
MDCK Permeability:	1.3088214473100379e-05
Pgp-inhibitor:	0.995
Pgp-substrate:	0.92
Human Intestinal Absorption (HIA):	0.006
20% Bioavailability (F20%):	0.952
30% Bioavailability (F30%):	0.452

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.108
Plasma Protein Binding (PPB):	96.7901840209961%
Volume Distribution (VD):	1.368
Pgp-substrate:	2.007864475250244%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.573
CYP2C19-inhibitor:	0.05
CYP2C19-substrate:	0.94
CYP2C9-inhibitor:	0.168
CYP2C9-substrate:	0.055
CYP2D6-inhibitor:	0.009
CYP2D6-substrate:	0.142
CYP3A4-inhibitor:	0.414
CYP3A4-substrate:	0.779

ADMET: Excretion

Clearance (CL):	8.17
Half-life (T1/2):	0.088

ADMET: Toxicity

hERG Blockers:	0.482
Human Hepatotoxicity (H-HT):	0.188
Drug-inuced Liver Injury (DILI):	0.171
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.096
Maximum Recommended Daily Dose:	0.042
Skin Sensitization:	0.346
Carcinogencity:	0.039
Eye Corrosion:	0.005
Eye Irritation:	0.043
Respiratory Toxicity:	0.848

Download Data

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

Natural Product: NPC474759

Natural Product ID:	NPC474759
*Common Name:**	Schleicherastatin 3
IUPAC Name:	(3S,7R,8S,9S,10R,13R,14S)-17-[(2S,3R,5R)-3-hydroxy-5,6-dimethylheptan-2-yl]-7-methoxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	Schleicherastatin 3
Standard InCHIKey:	UYEMZAOCHUCHMG-GVTGRELXSA-N
Standard InCHI:	InChI=1S/C29H50O3/c1-17(2)18(3)14-25(31)19(4)22-8-9-23-27-24(11-13-29(22,23)6)28(5)12-10-21(30)15-20(28)16-26(27)32-7/h16-19,21-27,30-31H,8-15H2,1-7H3/t18-,19+,21+,22?,23+,24+,25-,26+,27+,28+,29-/m1/s1
SMILES:	CC(C)C(C)CC(C(C)C1CCC2C1(CCC3C2C(C=C4C3(CCC(C4)O)C)OC)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL481654
PubChem CID:	44575191
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 [CHEMONTID:0002194] Hydroxy bile acids, alcohols and derivatives [CHEMONTID:0000516] Dihydroxy 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
NPO33309	schleichera oleosa	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10650082]

☑ 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
GI50	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	GI50	=	1.2	ug.mL-1	PMID[464760]

☑ 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 NPC474759 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	155
0.1-0.2	1293
0.2-0.3	4924
0.3-0.4	15259
0.4-0.5	8524
0.5-0.6	6192
0.6-0.7	4658
0.7-0.8	1365
0.8-0.85	204
0.85-0.9	56
0.9-0.95	57
0.95-1	10

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474683
1.0	High Similarity	NPC7505
1.0	High Similarity	NPC474752
1.0	High Similarity	NPC474731
1.0	High Similarity	NPC82986
0.961	High Similarity	NPC470049
0.9494	High Similarity	NPC274448
0.9494	High Similarity	NPC266511
0.9494	High Similarity	NPC157257
0.9474	High Similarity	NPC28862
0.9474	High Similarity	NPC81306
0.9474	High Similarity	NPC109546
0.9474	High Similarity	NPC84694
0.9474	High Similarity	NPC47982
0.9474	High Similarity	NPC143182
0.9367	High Similarity	NPC470077
0.9351	High Similarity	NPC234193
0.9342	High Similarity	NPC473943
0.9342	High Similarity	NPC474216
0.9333	High Similarity	NPC107059
0.9333	High Similarity	NPC321381
0.9333	High Similarity	NPC321016
0.9259	High Similarity	NPC149224
0.9241	High Similarity	NPC475789
0.9231	High Similarity	NPC264245
0.9231	High Similarity	NPC209620
0.9231	High Similarity	NPC47761
0.9231	High Similarity	NPC23852
0.9221	High Similarity	NPC30986
0.9221	High Similarity	NPC209430
0.9211	High Similarity	NPC155986
0.9211	High Similarity	NPC198968
0.9211	High Similarity	NPC318495
0.92	High Similarity	NPC288035
0.92	High Similarity	NPC134847
0.92	High Similarity	NPC285893
0.92	High Similarity	NPC28657
0.92	High Similarity	NPC136188
0.92	High Similarity	NPC304309
0.92	High Similarity	NPC22105
0.92	High Similarity	NPC230301
0.92	High Similarity	NPC162742
0.9114	High Similarity	NPC50964
0.9114	High Similarity	NPC101462
0.9114	High Similarity	NPC189972
0.9114	High Similarity	NPC49964
0.9103	High Similarity	NPC241290
0.9103	High Similarity	NPC209944
0.9103	High Similarity	NPC164840
0.9091	High Similarity	NPC477522
0.9091	High Similarity	NPC87604
0.9079	High Similarity	NPC247325
0.9079	High Similarity	NPC300324
0.9079	High Similarity	NPC113733
0.9079	High Similarity	NPC244488
0.9079	High Similarity	NPC240604
0.9	High Similarity	NPC474634
0.9	High Similarity	NPC317458
0.9	High Similarity	NPC470558
0.8974	High Similarity	NPC328714
0.8961	High Similarity	NPC34019
0.8947	High Similarity	NPC257347
0.8947	High Similarity	NPC141071
0.8947	High Similarity	NPC471723
0.8929	High Similarity	NPC295668
0.8916	High Similarity	NPC471952
0.8889	High Similarity	NPC474047
0.8889	High Similarity	NPC185568
0.8889	High Similarity	NPC205845
0.8875	High Similarity	NPC5985
0.8861	High Similarity	NPC26117
0.8846	High Similarity	NPC76931
0.8846	High Similarity	NPC477514
0.8846	High Similarity	NPC18603
0.8846	High Similarity	NPC275910
0.8846	High Similarity	NPC307965
0.8831	High Similarity	NPC129165
0.8831	High Similarity	NPC134330
0.8831	High Similarity	NPC189883
0.8831	High Similarity	NPC96319
0.8824	High Similarity	NPC234335
0.875	High Similarity	NPC474531
0.875	High Similarity	NPC470383
0.8734	High Similarity	NPC1319
0.8718	High Similarity	NPC214570
0.8684	High Similarity	NPC474140
0.8684	High Similarity	NPC471799
0.8675	High Similarity	NPC293287
0.8675	High Similarity	NPC152808
0.8675	High Similarity	NPC6391
0.8675	High Similarity	NPC261266
0.8659	High Similarity	NPC238485
0.8642	High Similarity	NPC304285
0.8642	High Similarity	NPC296701
0.8642	High Similarity	NPC87489
0.8642	High Similarity	NPC202389
0.8642	High Similarity	NPC470614
0.8642	High Similarity	NPC1272
0.8642	High Similarity	NPC218616
0.8625	High Similarity	NPC236112
0.8621	High Similarity	NPC127718
0.8621	High Similarity	NPC65402
0.8608	High Similarity	NPC167037
0.8608	High Similarity	NPC476314
0.8608	High Similarity	NPC83351
0.8608	High Similarity	NPC138621
0.8608	High Similarity	NPC167891
0.8608	High Similarity	NPC244385
0.8608	High Similarity	NPC6978
0.8608	High Similarity	NPC285761
0.8605	High Similarity	NPC471453
0.859	High Similarity	NPC470362
0.859	High Similarity	NPC73875
0.859	High Similarity	NPC237460
0.859	High Similarity	NPC46160
0.859	High Similarity	NPC202642
0.8571	High Similarity	NPC469593
0.8571	High Similarity	NPC469534
0.8571	High Similarity	NPC469533
0.8571	High Similarity	NPC471797
0.8554	High Similarity	NPC474349
0.8554	High Similarity	NPC474189
0.8554	High Similarity	NPC318390
0.8537	High Similarity	NPC470384
0.8523	High Similarity	NPC8774
0.8506	High Similarity	NPC307776
0.85	High Similarity	NPC80530
0.85	High Similarity	NPC273410
0.8481	Intermediate Similarity	NPC91594
0.8471	Intermediate Similarity	NPC474668
0.8462	Intermediate Similarity	NPC322353
0.8462	Intermediate Similarity	NPC118508
0.8462	Intermediate Similarity	NPC121744
0.8452	Intermediate Similarity	NPC474970
0.8434	Intermediate Similarity	NPC59453
0.8434	Intermediate Similarity	NPC221758
0.8434	Intermediate Similarity	NPC33913
0.8434	Intermediate Similarity	NPC124172
0.8434	Intermediate Similarity	NPC209802
0.8434	Intermediate Similarity	NPC472265
0.8434	Intermediate Similarity	NPC231310
0.8427	Intermediate Similarity	NPC288970
0.8427	Intermediate Similarity	NPC98457
0.8427	Intermediate Similarity	NPC78473
0.8427	Intermediate Similarity	NPC227583
0.8427	Intermediate Similarity	NPC12103
0.8421	Intermediate Similarity	NPC34834
0.8415	Intermediate Similarity	NPC248886
0.8415	Intermediate Similarity	NPC155521
0.8415	Intermediate Similarity	NPC30166
0.8415	Intermediate Similarity	NPC201852
0.8409	Intermediate Similarity	NPC144202
0.84	Intermediate Similarity	NPC160209
0.84	Intermediate Similarity	NPC208999
0.8395	Intermediate Similarity	NPC102253
0.8395	Intermediate Similarity	NPC322313
0.8395	Intermediate Similarity	NPC236237
0.8395	Intermediate Similarity	NPC13554
0.8391	Intermediate Similarity	NPC177641
0.8375	Intermediate Similarity	NPC65897
0.8375	Intermediate Similarity	NPC186191
0.8375	Intermediate Similarity	NPC302041
0.8375	Intermediate Similarity	NPC85346
0.8375	Intermediate Similarity	NPC205455
0.8372	Intermediate Similarity	NPC477606
0.8372	Intermediate Similarity	NPC146554
0.8372	Intermediate Similarity	NPC470361
0.8372	Intermediate Similarity	NPC473647
0.8333	Intermediate Similarity	NPC243342
0.8333	Intermediate Similarity	NPC471224
0.8333	Intermediate Similarity	NPC27395
0.8333	Intermediate Similarity	NPC470360
0.8333	Intermediate Similarity	NPC126815
0.8333	Intermediate Similarity	NPC291634
0.8333	Intermediate Similarity	NPC477138
0.8333	Intermediate Similarity	NPC329090
0.8313	Intermediate Similarity	NPC470047
0.8313	Intermediate Similarity	NPC82623
0.8313	Intermediate Similarity	NPC470046
0.8313	Intermediate Similarity	NPC134481
0.8312	Intermediate Similarity	NPC242001
0.8295	Intermediate Similarity	NPC27531
0.8293	Intermediate Similarity	NPC476646
0.8276	Intermediate Similarity	NPC11216
0.8276	Intermediate Similarity	NPC204188
0.8276	Intermediate Similarity	NPC329596
0.8276	Intermediate Similarity	NPC3345
0.8276	Intermediate Similarity	NPC48010
0.8276	Intermediate Similarity	NPC291484
0.8276	Intermediate Similarity	NPC80561
0.8272	Intermediate Similarity	NPC472463
0.8272	Intermediate Similarity	NPC153987
0.8272	Intermediate Similarity	NPC44083
0.8256	Intermediate Similarity	NPC133588
0.8256	Intermediate Similarity	NPC67872
0.825	Intermediate Similarity	NPC471798
0.825	Intermediate Similarity	NPC470758
0.825	Intermediate Similarity	NPC470711
0.8235	Intermediate Similarity	NPC477604
0.8235	Intermediate Similarity	NPC94462

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 NPC474759 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	152
0.1-0.2	1451
0.2-0.3	4073
0.3-0.4	2409
0.4-0.5	608
0.5-0.6	188
0.6-0.7	179
0.7-0.8	67
0.8-0.85	19
0.85-0.9	2
0.9-0.95	2
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.92	High Similarity	NPD6942	Approved
0.92	High Similarity	NPD7339	Approved
0.8831	High Similarity	NPD3701	Clinical (unspecified phase)
0.8434	Intermediate Similarity	NPD4786	Approved
0.8395	Intermediate Similarity	NPD7525	Registered
0.8353	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.8333	Intermediate Similarity	NPD6924	Approved
0.8333	Intermediate Similarity	NPD6926	Approved
0.8193	Intermediate Similarity	NPD3667	Approved
0.8125	Intermediate Similarity	NPD6933	Approved
0.8101	Intermediate Similarity	NPD4784	Approved
0.8101	Intermediate Similarity	NPD4785	Approved
0.8077	Intermediate Similarity	NPD7150	Approved
0.8077	Intermediate Similarity	NPD4243	Approved
0.8077	Intermediate Similarity	NPD7152	Approved
0.8077	Intermediate Similarity	NPD7151	Approved
0.8052	Intermediate Similarity	NPD6923	Approved
0.8052	Intermediate Similarity	NPD6922	Approved
0.8049	Intermediate Similarity	NPD6929	Approved
0.8049	Intermediate Similarity	NPD7645	Phase 2
0.7952	Intermediate Similarity	NPD6931	Approved
0.7952	Intermediate Similarity	NPD6930	Phase 2
0.7949	Intermediate Similarity	NPD7144	Approved
0.7949	Intermediate Similarity	NPD7143	Approved
0.7882	Intermediate Similarity	NPD6695	Phase 3
0.7805	Intermediate Similarity	NPD5776	Phase 2
0.7805	Intermediate Similarity	NPD6925	Approved
0.7791	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD5328	Approved
0.7753	Intermediate Similarity	NPD6051	Approved
0.7738	Intermediate Similarity	NPD4748	Discontinued
0.7738	Intermediate Similarity	NPD7514	Phase 3
0.7711	Intermediate Similarity	NPD7145	Approved
0.7711	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD6399	Phase 3
0.766	Intermediate Similarity	NPD7638	Approved
0.7647	Intermediate Similarity	NPD6902	Approved
0.7614	Intermediate Similarity	NPD3618	Phase 1
0.759	Intermediate Similarity	NPD6932	Approved
0.7586	Intermediate Similarity	NPD3665	Phase 1
0.7586	Intermediate Similarity	NPD3666	Approved
0.7586	Intermediate Similarity	NPD3133	Approved
0.7582	Intermediate Similarity	NPD6079	Approved
0.7579	Intermediate Similarity	NPD7640	Approved
0.7579	Intermediate Similarity	NPD7639	Approved
0.7561	Intermediate Similarity	NPD4190	Phase 3
0.7561	Intermediate Similarity	NPD8264	Approved
0.7561	Intermediate Similarity	NPD5275	Approved
0.7529	Intermediate Similarity	NPD7332	Phase 2
0.7529	Intermediate Similarity	NPD7509	Discontinued
0.7528	Intermediate Similarity	NPD7750	Discontinued
0.7528	Intermediate Similarity	NPD7524	Approved
0.75	Intermediate Similarity	NPD6893	Approved
0.7412	Intermediate Similarity	NPD4195	Approved
0.7412	Intermediate Similarity	NPD6683	Phase 2
0.7386	Intermediate Similarity	NPD3668	Phase 3
0.7312	Intermediate Similarity	NPD4202	Approved
0.7241	Intermediate Similarity	NPD6898	Phase 1
0.7222	Intermediate Similarity	NPD5279	Phase 3
0.7204	Intermediate Similarity	NPD7087	Discontinued
0.7174	Intermediate Similarity	NPD4753	Phase 2
0.7159	Intermediate Similarity	NPD4223	Phase 3
0.7159	Intermediate Similarity	NPD4221	Approved
0.7143	Intermediate Similarity	NPD4159	Approved
0.7111	Intermediate Similarity	NPD5329	Approved
0.7111	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD5222	Approved
0.7083	Intermediate Similarity	NPD4697	Phase 3
0.7083	Intermediate Similarity	NPD5221	Approved
0.7083	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD6409	Approved
0.7033	Intermediate Similarity	NPD7146	Approved
0.7033	Intermediate Similarity	NPD6684	Approved
0.7033	Intermediate Similarity	NPD5330	Approved
0.7033	Intermediate Similarity	NPD7521	Approved
0.7033	Intermediate Similarity	NPD7334	Approved
0.7021	Intermediate Similarity	NPD7637	Suspended
0.701	Intermediate Similarity	NPD5173	Approved
0.701	Intermediate Similarity	NPD4755	Approved
0.701	Intermediate Similarity	NPD6084	Phase 2
0.701	Intermediate Similarity	NPD6083	Phase 2
0.7009	Intermediate Similarity	NPD7115	Discovery
0.7	Intermediate Similarity	NPD4197	Approved
0.6939	Remote Similarity	NPD4225	Approved
0.69	Remote Similarity	NPD7632	Discontinued
0.69	Remote Similarity	NPD5211	Phase 2
0.6889	Remote Similarity	NPD4788	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6672	Approved
0.6882	Remote Similarity	NPD6903	Approved
0.6869	Remote Similarity	NPD5285	Approved
0.6869	Remote Similarity	NPD5286	Approved
0.6869	Remote Similarity	NPD4700	Approved
0.6869	Remote Similarity	NPD4696	Approved
0.6863	Remote Similarity	NPD6402	Approved
0.6863	Remote Similarity	NPD7128	Approved
0.6863	Remote Similarity	NPD5739	Approved
0.6863	Remote Similarity	NPD6675	Approved
0.6848	Remote Similarity	NPD5205	Approved
0.6848	Remote Similarity	NPD4138	Approved
0.6848	Remote Similarity	NPD4689	Approved
0.6848	Remote Similarity	NPD4688	Approved
0.6848	Remote Similarity	NPD4690	Approved
0.6848	Remote Similarity	NPD4693	Phase 3
0.6842	Remote Similarity	NPD7515	Phase 2
0.6804	Remote Similarity	NPD4629	Approved
0.6804	Remote Similarity	NPD5210	Approved
0.68	Remote Similarity	NPD5223	Approved
0.6768	Remote Similarity	NPD5290	Discontinued
0.6765	Remote Similarity	NPD5141	Approved
0.6747	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5224	Approved
0.6733	Remote Similarity	NPD5225	Approved
0.6733	Remote Similarity	NPD5226	Approved
0.6733	Remote Similarity	NPD4633	Approved
0.6731	Remote Similarity	NPD7320	Approved
0.6731	Remote Similarity	NPD6881	Approved
0.6731	Remote Similarity	NPD6899	Approved
0.6709	Remote Similarity	NPD368	Approved
0.6705	Remote Similarity	NPD3617	Approved
0.6702	Remote Similarity	NPD4723	Approved
0.6702	Remote Similarity	NPD4722	Approved
0.6701	Remote Similarity	NPD7748	Approved
0.6667	Remote Similarity	NPD5690	Phase 2
0.6667	Remote Similarity	NPD5280	Approved
0.6667	Remote Similarity	NPD4787	Phase 1
0.6667	Remote Similarity	NPD4754	Approved
0.6667	Remote Similarity	NPD6372	Approved
0.6667	Remote Similarity	NPD8035	Phase 2
0.6667	Remote Similarity	NPD4623	Approved
0.6667	Remote Similarity	NPD8034	Phase 2
0.6667	Remote Similarity	NPD5175	Approved
0.6667	Remote Similarity	NPD4694	Approved
0.6667	Remote Similarity	NPD6373	Approved
0.6667	Remote Similarity	NPD4519	Discontinued
0.6667	Remote Similarity	NPD5693	Phase 1
0.6667	Remote Similarity	NPD6098	Approved
0.6667	Remote Similarity	NPD5174	Approved
0.6636	Remote Similarity	NPD7327	Approved
0.6636	Remote Similarity	NPD7328	Approved
0.6635	Remote Similarity	NPD5701	Approved
0.6635	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD5695	Phase 3
0.663	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6607	Remote Similarity	NPD8033	Approved
0.6604	Remote Similarity	NPD7102	Approved
0.6604	Remote Similarity	NPD6883	Approved
0.6604	Remote Similarity	NPD7290	Approved
0.66	Remote Similarity	NPD5696	Approved
0.6593	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6588	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD342	Phase 1
0.6577	Remote Similarity	NPD7516	Approved
0.6571	Remote Similarity	NPD6011	Approved
0.6562	Remote Similarity	NPD7136	Phase 2
0.6559	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD4695	Discontinued
0.6542	Remote Similarity	NPD6847	Approved
0.6542	Remote Similarity	NPD6649	Approved
0.6542	Remote Similarity	NPD6650	Approved
0.6542	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD8130	Phase 1
0.6542	Remote Similarity	NPD6869	Approved
0.6542	Remote Similarity	NPD6617	Approved
0.6538	Remote Similarity	NPD6640	Phase 3
0.6538	Remote Similarity	NPD4767	Approved
0.6538	Remote Similarity	NPD4768	Approved
0.6522	Remote Similarity	NPD5362	Discontinued
0.6518	Remote Similarity	NPD8294	Approved
0.6518	Remote Similarity	NPD8377	Approved
0.6517	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD6014	Approved
0.6509	Remote Similarity	NPD6012	Approved
0.6509	Remote Similarity	NPD6013	Approved
0.65	Remote Similarity	NPD7902	Approved
0.6489	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD4692	Approved
0.6484	Remote Similarity	NPD4139	Approved
0.6481	Remote Similarity	NPD8297	Approved
0.6481	Remote Similarity	NPD6053	Discontinued
0.6481	Remote Similarity	NPD6882	Approved
0.6476	Remote Similarity	NPD6412	Phase 2
0.6471	Remote Similarity	NPD4747	Approved
0.646	Remote Similarity	NPD8378	Approved
0.646	Remote Similarity	NPD8335	Approved
0.646	Remote Similarity	NPD8296	Approved
0.646	Remote Similarity	NPD7503	Approved
0.646	Remote Similarity	NPD8380	Approved
0.646	Remote Similarity	NPD8379	Approved
0.6458	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD6673	Approved
0.6437	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD6686	Approved
0.6415	Remote Similarity	NPD5128	Approved
0.6415	Remote Similarity	NPD4729	Approved
0.6415	Remote Similarity	NPD5168	Approved
0.6415	Remote Similarity	NPD4730	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