NPASS Compound

Structure

NPC87489 OpenBabel07101718322D 33 36 0 0 1 0 0 0 0 0999 V2000 2.2382 2.4680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9792 6.0914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2361 5.4223 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 -2.9641 -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 -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 1.5388 0.5000 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 0.9000 3.9543 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 1.8781 4.1622 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 0.9511 -0.3090 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 1.2601 2.2601 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 -1.7321 0.0000 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 0.5909 3.0032 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 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1871 5.1132 0.0000 C 0 0 0 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 1 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 -0.3872 2.7953 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 3.1653 5.3212 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2 26 1 0 0 0 0 3 26 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 22 1 0 0 0 0 10 24 1 0 0 0 0 11 17 1 0 0 0 0 11 20 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 15 2 0 0 0 0 13 23 1 0 0 0 0 14 16 1 0 0 0 0 14 25 1 0 0 0 0 15 26 1 0 0 0 0 16 28 1 0 0 0 0 17 30 1 0 0 0 0 18 29 1 0 0 0 0 19 1 1 1 0 0 0 19 20 1 0 0 0 0 19 23 1 0 0 0 0 20 29 1 1 0 0 0 21 22 2 0 0 0 0 21 28 1 0 0 0 0 22 30 1 0 0 0 0 23 31 1 6 0 0 0 24 27 1 0 0 0 0 24 28 1 1 0 0 0 25 27 1 0 0 0 0 25 32 1 1 0 0 0 26 33 1 0 0 0 0 28 6 1 1 0 0 0 29 30 1 1 0 0 0 30 8 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	458.38
Volume:	514.308
LogP:	4.949
LogD:	4.35
LogS:	-4.848
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.426
Synthetic Accessibility Score:	4.974
Fsp3:	0.867
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:	-4.822
MDCK Permeability:	2.077183307847008e-05
Pgp-inhibitor:	0.839
Pgp-substrate:	0.014
Human Intestinal Absorption (HIA):	0.016
20% Bioavailability (F20%):	0.097
30% Bioavailability (F30%):	0.448

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.133
Plasma Protein Binding (PPB):	88.66236877441406%
Volume Distribution (VD):	1.05
Pgp-substrate:	0.9419195652008057%

ADMET: Metabolism

CYP1A2-inhibitor:	0.013
CYP1A2-substrate:	0.512
CYP2C19-inhibitor:	0.078
CYP2C19-substrate:	0.955
CYP2C9-inhibitor:	0.224
CYP2C9-substrate:	0.711
CYP2D6-inhibitor:	0.024
CYP2D6-substrate:	0.724
CYP3A4-inhibitor:	0.618
CYP3A4-substrate:	0.697

ADMET: Excretion

Clearance (CL):	5.677
Half-life (T1/2):	0.125

ADMET: Toxicity

hERG Blockers:	0.028
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.016
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.379
Maximum Recommended Daily Dose:	0.97
Skin Sensitization:	0.428
Carcinogencity:	0.026
Eye Corrosion:	0.005
Eye Irritation:	0.049
Respiratory Toxicity:	0.832

Download Data

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

Natural Product: NPC87489

Natural Product ID:	NPC87489
*Common Name:**	Lanosta-8,23E-Diene-3Beta,22R,25-Triol
IUPAC Name:	(E,5R,6S)-6-[(3S,5R,10S,13R,14R,17R)-3-hydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-3-ene-2,5-diol
Synonyms:
Standard InCHIKey:	KIWHRCNGJTUEHJ-IBDCHPIJSA-N
Standard InCHI:	InChI=1S/C30H50O3/c1-19(23(31)13-15-26(2,3)33)20-11-17-30(8)22-9-10-24-27(4,5)25(32)14-16-28(24,6)21(22)12-18-29(20,30)7/h13,15,19-20,23-25,31-33H,9-12,14,16-18H2,1-8H3/b15-13+/t19-,20+,23+,24-,25-,28+,29+,30-/m0/s1
SMILES:	O[C@@H]([C@H]([C@H]1CC[C@@]2([C@]1(C)CCC1=C2CC[C@@H]2[C@]1(C)CC[C@@H](C2(C)C)O)C)C)/C=C/C(O)(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL456462
PubChem CID:	44581566
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
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[17049251]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	sclerotia	n.a.	n.a.	PMID[18387711]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24359303]
NPO18766	Inonotus obliquus	Species	Hymenochaetaceae	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
IC50	1
Others	5

Activity Type	# Activity
Cell Line	1
Others	5

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT80	Cell Line	Raji	Homo sapiens	Activity	=	70.0	%	PMID[550399]
NPT2	Others	Unspecified		Activity	=	89.2	%	PMID[550399]
NPT2	Others	Unspecified		Activity	=	0.0	%	PMID[550399]
NPT2	Others	Unspecified		Activity	=	69.8	%	PMID[550399]
NPT2	Others	Unspecified		IC50	=	231.0	molar ratio	PMID[550399]
NPT2	Others	Unspecified		Activity	=	26.9	%	PMID[550399]

☑ 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 NPC87489 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	145
0.1-0.2	1261
0.2-0.3	5581
0.3-0.4	15676
0.4-0.5	8824
0.5-0.6	6179
0.6-0.7	3608
0.7-0.8	1141
0.8-0.85	183
0.85-0.9	79
0.9-0.95	16
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9744	High Similarity	NPC231310
0.9494	High Similarity	NPC238485
0.9487	High Similarity	NPC202389
0.9487	High Similarity	NPC296701
0.9487	High Similarity	NPC49964
0.9487	High Similarity	NPC218616
0.9359	High Similarity	NPC264245
0.9351	High Similarity	NPC30986
0.9351	High Similarity	NPC209430
0.9342	High Similarity	NPC214570
0.9259	High Similarity	NPC261266
0.925	High Similarity	NPC470077
0.925	High Similarity	NPC205845
0.9231	High Similarity	NPC241290
0.9231	High Similarity	NPC209944
0.9231	High Similarity	NPC164840
0.9231	High Similarity	NPC234193
0.9221	High Similarity	NPC275910
0.9211	High Similarity	NPC46160
0.9211	High Similarity	NPC202642
0.9211	High Similarity	NPC470362
0.9211	High Similarity	NPC73875
0.9136	High Similarity	NPC470360
0.9136	High Similarity	NPC274448
0.9136	High Similarity	NPC318390
0.9125	High Similarity	NPC470384
0.9125	High Similarity	NPC82623
0.9114	High Similarity	NPC47761
0.9103	High Similarity	NPC109546
0.9103	High Similarity	NPC143182
0.9103	High Similarity	NPC84694
0.9103	High Similarity	NPC28862
0.9103	High Similarity	NPC47982
0.9103	High Similarity	NPC81306
0.9079	High Similarity	NPC118508
0.9079	High Similarity	NPC322353
0.9079	High Similarity	NPC121744
0.9036	High Similarity	NPC133588
0.9024	High Similarity	NPC299068
0.9024	High Similarity	NPC6391
0.9012	High Similarity	NPC474047
0.9	High Similarity	NPC101462
0.9	High Similarity	NPC470049
0.9	High Similarity	NPC50964
0.8974	High Similarity	NPC186191
0.8974	High Similarity	NPC285761
0.8974	High Similarity	NPC474216
0.8974	High Similarity	NPC205455
0.8961	High Similarity	NPC244488
0.8961	High Similarity	NPC134330
0.8961	High Similarity	NPC129165
0.8961	High Similarity	NPC189883
0.8961	High Similarity	NPC265588
0.8961	High Similarity	NPC247325
0.8916	High Similarity	NPC149224
0.8902	High Similarity	NPC157257
0.8889	High Similarity	NPC134481
0.8889	High Similarity	NPC470558
0.8889	High Similarity	NPC317458
0.8889	High Similarity	NPC474634
0.8889	High Similarity	NPC475789
0.8875	High Similarity	NPC6707
0.8875	High Similarity	NPC209620
0.8875	High Similarity	NPC23852
0.8861	High Similarity	NPC1319
0.8861	High Similarity	NPC80530
0.8861	High Similarity	NPC273410
0.8846	High Similarity	NPC470758
0.8846	High Similarity	NPC318495
0.8846	High Similarity	NPC91594
0.8846	High Similarity	NPC155986
0.8846	High Similarity	NPC198968
0.8846	High Similarity	NPC470711
0.8837	High Similarity	NPC310013
0.8831	High Similarity	NPC141071
0.8831	High Similarity	NPC471723
0.8831	High Similarity	NPC257347
0.8824	High Similarity	NPC245410
0.8824	High Similarity	NPC192437
0.8824	High Similarity	NPC3345
0.8824	High Similarity	NPC329596
0.8824	High Similarity	NPC80561
0.8824	High Similarity	NPC470390
0.8824	High Similarity	NPC295668
0.8824	High Similarity	NPC11216
0.8824	High Similarity	NPC204188
0.8824	High Similarity	NPC270511
0.8824	High Similarity	NPC291484
0.8816	High Similarity	NPC201373
0.881	High Similarity	NPC280556
0.878	High Similarity	NPC185568
0.8765	High Similarity	NPC189972
0.8765	High Similarity	NPC201852
0.8765	High Similarity	NPC30166
0.875	High Similarity	NPC102253
0.875	High Similarity	NPC13554
0.875	High Similarity	NPC236237
0.875	High Similarity	NPC322313
0.875	High Similarity	NPC236112
0.8734	High Similarity	NPC167037
0.8734	High Similarity	NPC473943
0.8734	High Similarity	NPC11908
0.8734	High Similarity	NPC244385
0.8734	High Similarity	NPC318136
0.8734	High Similarity	NPC6978
0.8734	High Similarity	NPC138621
0.8721	High Similarity	NPC41554
0.8721	High Similarity	NPC97404
0.8718	High Similarity	NPC300324
0.8718	High Similarity	NPC113733
0.8718	High Similarity	NPC321016
0.8718	High Similarity	NPC321381
0.8718	High Similarity	NPC240604
0.8718	High Similarity	NPC237460
0.8718	High Similarity	NPC107059
0.8718	High Similarity	NPC470749
0.8706	High Similarity	NPC470361
0.8701	High Similarity	NPC476366
0.8701	High Similarity	NPC201048
0.8701	High Similarity	NPC469534
0.8701	High Similarity	NPC469533
0.8701	High Similarity	NPC469593
0.8684	High Similarity	NPC110799
0.8675	High Similarity	NPC266511
0.8642	High Similarity	NPC476646
0.8642	High Similarity	NPC249423
0.8642	High Similarity	NPC474531
0.8642	High Similarity	NPC474683
0.8642	High Similarity	NPC474752
0.8642	High Similarity	NPC474731
0.8642	High Similarity	NPC7505
0.8642	High Similarity	NPC82986
0.8642	High Similarity	NPC474759
0.8636	High Similarity	NPC259286
0.8625	High Similarity	NPC328714
0.8605	High Similarity	NPC14380
0.859	High Similarity	NPC285893
0.859	High Similarity	NPC304309
0.859	High Similarity	NPC230301
0.859	High Similarity	NPC162742
0.859	High Similarity	NPC134847
0.859	High Similarity	NPC288035
0.859	High Similarity	NPC22105
0.859	High Similarity	NPC185536
0.859	High Similarity	NPC28657
0.859	High Similarity	NPC136188
0.8588	High Similarity	NPC474668
0.8571	High Similarity	NPC474140
0.8571	High Similarity	NPC152808
0.8571	High Similarity	NPC182717
0.8571	High Similarity	NPC139724
0.8571	High Similarity	NPC293287
0.8554	High Similarity	NPC15534
0.8553	High Similarity	NPC34834
0.8539	High Similarity	NPC249954
0.8537	High Similarity	NPC20853
0.8523	High Similarity	NPC144202
0.8519	High Similarity	NPC96362
0.8519	High Similarity	NPC22403
0.8519	High Similarity	NPC295131
0.8506	High Similarity	NPC475806
0.8506	High Similarity	NPC212948
0.85	High Similarity	NPC472342
0.85	High Similarity	NPC87604
0.85	High Similarity	NPC302041
0.85	High Similarity	NPC301707
0.85	High Similarity	NPC307965
0.85	High Similarity	NPC477514
0.85	High Similarity	NPC83351
0.85	High Similarity	NPC167891
0.85	High Similarity	NPC18603
0.85	High Similarity	NPC85346
0.85	High Similarity	NPC477522
0.85	High Similarity	NPC65897
0.85	High Similarity	NPC76931
0.8488	Intermediate Similarity	NPC262858
0.8488	Intermediate Similarity	NPC472240
0.8488	Intermediate Similarity	NPC101886
0.8481	Intermediate Similarity	NPC253190
0.8471	Intermediate Similarity	NPC470620
0.8462	Intermediate Similarity	NPC243342
0.8462	Intermediate Similarity	NPC477138
0.8462	Intermediate Similarity	NPC91858
0.8452	Intermediate Similarity	NPC474083
0.8444	Intermediate Similarity	NPC261807
0.8442	Intermediate Similarity	NPC167706
0.8442	Intermediate Similarity	NPC23954
0.8434	Intermediate Similarity	NPC477818
0.8434	Intermediate Similarity	NPC207013
0.8421	Intermediate Similarity	NPC471560
0.8415	Intermediate Similarity	NPC470383
0.8409	Intermediate Similarity	NPC214697
0.8409	Intermediate Similarity	NPC27531
0.8409	Intermediate Similarity	NPC69454
0.8391	Intermediate Similarity	NPC469400
0.8375	Intermediate Similarity	NPC212241
0.8375	Intermediate Similarity	NPC119355
0.8375	Intermediate Similarity	NPC34019
0.8375	Intermediate Similarity	NPC331618
0.8375	Intermediate Similarity	NPC248830

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 NPC87489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	146
0.1-0.2	1530
0.2-0.3	4275
0.3-0.4	2265
0.4-0.5	507
0.5-0.6	190
0.6-0.7	169
0.7-0.8	63
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.875	High Similarity	NPD7525	Registered
0.859	High Similarity	NPD6942	Approved
0.859	High Similarity	NPD7339	Approved
0.8256	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.825	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.8125	Intermediate Similarity	NPD8264	Approved
0.8072	Intermediate Similarity	NPD4748	Discontinued
0.8	Intermediate Similarity	NPD4785	Approved
0.8	Intermediate Similarity	NPD4784	Approved
0.8	Intermediate Similarity	NPD6924	Approved
0.8	Intermediate Similarity	NPD6926	Approved
0.7975	Intermediate Similarity	NPD4243	Approved
0.7952	Intermediate Similarity	NPD7645	Phase 2
0.7907	Intermediate Similarity	NPD4786	Approved
0.7889	Intermediate Similarity	NPD6079	Approved
0.7865	Intermediate Similarity	NPD5328	Approved
0.7857	Intermediate Similarity	NPD6931	Approved
0.7857	Intermediate Similarity	NPD7514	Phase 3
0.7857	Intermediate Similarity	NPD6930	Phase 2
0.7831	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7805	Intermediate Similarity	NPD6933	Approved
0.775	Intermediate Similarity	NPD7152	Approved
0.775	Intermediate Similarity	NPD7150	Approved
0.775	Intermediate Similarity	NPD7151	Approved
0.7738	Intermediate Similarity	NPD6929	Approved
0.7727	Intermediate Similarity	NPD3618	Phase 1
0.7674	Intermediate Similarity	NPD3667	Approved
0.7647	Intermediate Similarity	NPD7332	Phase 2
0.7625	Intermediate Similarity	NPD7143	Approved
0.7625	Intermediate Similarity	NPD7144	Approved
0.7619	Intermediate Similarity	NPD7145	Approved
0.7609	Intermediate Similarity	NPD4202	Approved
0.7586	Intermediate Similarity	NPD6695	Phase 3
0.7558	Intermediate Similarity	NPD6902	Approved
0.7529	Intermediate Similarity	NPD4195	Approved
0.7526	Intermediate Similarity	NPD5211	Phase 2
0.75	Intermediate Similarity	NPD6932	Approved
0.75	Intermediate Similarity	NPD6922	Approved
0.75	Intermediate Similarity	NPD6925	Approved
0.75	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD6923	Approved
0.75	Intermediate Similarity	NPD5776	Phase 2
0.747	Intermediate Similarity	NPD4190	Phase 3
0.747	Intermediate Similarity	NPD5275	Approved
0.7442	Intermediate Similarity	NPD7509	Discontinued
0.7416	Intermediate Similarity	NPD6893	Approved
0.7374	Intermediate Similarity	NPD5141	Approved
0.7368	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5221	Approved
0.7368	Intermediate Similarity	NPD5222	Approved
0.7333	Intermediate Similarity	NPD5279	Phase 3
0.732	Intermediate Similarity	NPD7639	Approved
0.732	Intermediate Similarity	NPD5285	Approved
0.732	Intermediate Similarity	NPD5286	Approved
0.732	Intermediate Similarity	NPD7640	Approved
0.732	Intermediate Similarity	NPD4696	Approved
0.7303	Intermediate Similarity	NPD3666	Approved
0.7303	Intermediate Similarity	NPD3133	Approved
0.7303	Intermediate Similarity	NPD3665	Phase 1
0.7292	Intermediate Similarity	NPD4755	Approved
0.7292	Intermediate Similarity	NPD5173	Approved
0.7273	Intermediate Similarity	NPD368	Approved
0.7253	Intermediate Similarity	NPD7750	Discontinued
0.7253	Intermediate Similarity	NPD7524	Approved
0.7245	Intermediate Similarity	NPD5223	Approved
0.7222	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD7638	Approved
0.7188	Intermediate Similarity	NPD4697	Phase 3
0.7172	Intermediate Similarity	NPD4633	Approved
0.7172	Intermediate Similarity	NPD5226	Approved
0.7172	Intermediate Similarity	NPD5225	Approved
0.7172	Intermediate Similarity	NPD5224	Approved
0.7159	Intermediate Similarity	NPD6898	Phase 1
0.7143	Intermediate Similarity	NPD4700	Approved
0.7143	Intermediate Similarity	NPD5690	Phase 2
0.7126	Intermediate Similarity	NPD6683	Phase 2
0.71	Intermediate Similarity	NPD5175	Approved
0.71	Intermediate Similarity	NPD5174	Approved
0.7097	Intermediate Similarity	NPD4753	Phase 2
0.7097	Intermediate Similarity	NPD6051	Approved
0.7079	Intermediate Similarity	NPD4223	Phase 3
0.7079	Intermediate Similarity	NPD4221	Approved
0.7073	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD6399	Phase 3
0.7041	Intermediate Similarity	NPD5290	Discontinued
0.7033	Intermediate Similarity	NPD5329	Approved
0.699	Remote Similarity	NPD6881	Approved
0.699	Remote Similarity	NPD6899	Approved
0.6961	Remote Similarity	NPD5739	Approved
0.6961	Remote Similarity	NPD7128	Approved
0.6961	Remote Similarity	NPD6675	Approved
0.6961	Remote Similarity	NPD6402	Approved
0.6957	Remote Similarity	NPD4623	Approved
0.6957	Remote Similarity	NPD5280	Approved
0.6957	Remote Similarity	NPD4519	Discontinued
0.6957	Remote Similarity	NPD4694	Approved
0.6947	Remote Similarity	NPD7087	Discontinued
0.6947	Remote Similarity	NPD7515	Phase 2
0.6944	Remote Similarity	NPD7115	Discovery
0.6931	Remote Similarity	NPD4754	Approved
0.6923	Remote Similarity	NPD4197	Approved
0.6923	Remote Similarity	NPD3668	Phase 3
0.6907	Remote Similarity	NPD5210	Approved
0.6907	Remote Similarity	NPD4629	Approved
0.6893	Remote Similarity	NPD5697	Approved
0.6857	Remote Similarity	NPD6883	Approved
0.6857	Remote Similarity	NPD7290	Approved
0.6857	Remote Similarity	NPD7102	Approved
0.6827	Remote Similarity	NPD6011	Approved
0.6827	Remote Similarity	NPD7320	Approved
0.6827	Remote Similarity	NPD4729	Approved
0.6827	Remote Similarity	NPD4730	Approved
0.6818	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD4788	Approved
0.6796	Remote Similarity	NPD4768	Approved
0.6796	Remote Similarity	NPD4767	Approved
0.6792	Remote Similarity	NPD6847	Approved
0.6792	Remote Similarity	NPD6617	Approved
0.6792	Remote Similarity	NPD6650	Approved
0.6792	Remote Similarity	NPD6869	Approved
0.6792	Remote Similarity	NPD8130	Phase 1
0.6792	Remote Similarity	NPD6649	Approved
0.6786	Remote Similarity	NPD4787	Phase 1
0.6778	Remote Similarity	NPD4139	Approved
0.6778	Remote Similarity	NPD4692	Approved
0.6774	Remote Similarity	NPD4138	Approved
0.6774	Remote Similarity	NPD4688	Approved
0.6774	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD5205	Approved
0.6774	Remote Similarity	NPD4693	Phase 3
0.6774	Remote Similarity	NPD4689	Approved
0.6774	Remote Similarity	NPD4690	Approved
0.6771	Remote Similarity	NPD7637	Suspended
0.6771	Remote Similarity	NPD5281	Approved
0.6771	Remote Similarity	NPD5284	Approved
0.6768	Remote Similarity	NPD6084	Phase 2
0.6768	Remote Similarity	NPD6083	Phase 2
0.6762	Remote Similarity	NPD6373	Approved
0.6762	Remote Similarity	NPD6372	Approved
0.6762	Remote Similarity	NPD6013	Approved
0.6762	Remote Similarity	NPD6014	Approved
0.6762	Remote Similarity	NPD6012	Approved
0.6735	Remote Similarity	NPD5695	Phase 3
0.6733	Remote Similarity	NPD4159	Approved
0.6731	Remote Similarity	NPD5701	Approved
0.6729	Remote Similarity	NPD8297	Approved
0.6729	Remote Similarity	NPD6882	Approved
0.6711	Remote Similarity	NPD342	Phase 1
0.6698	Remote Similarity	NPD5251	Approved
0.6698	Remote Similarity	NPD5249	Phase 3
0.6698	Remote Similarity	NPD4634	Approved
0.6698	Remote Similarity	NPD5247	Approved
0.6698	Remote Similarity	NPD5250	Approved
0.6698	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD5248	Approved
0.6698	Remote Similarity	NPD5135	Approved
0.6698	Remote Similarity	NPD5169	Approved
0.6667	Remote Similarity	NPD5128	Approved
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD5168	Approved
0.6636	Remote Similarity	NPD5216	Approved
0.6636	Remote Similarity	NPD5217	Approved
0.6636	Remote Similarity	NPD5127	Approved
0.6636	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5215	Approved
0.6633	Remote Similarity	NPD7748	Approved
0.6632	Remote Similarity	NPD4723	Approved
0.6632	Remote Similarity	NPD4722	Approved
0.6598	Remote Similarity	NPD8034	Phase 2
0.6598	Remote Similarity	NPD8035	Phase 2
0.6596	Remote Similarity	NPD7334	Approved
0.6596	Remote Similarity	NPD7521	Approved
0.6596	Remote Similarity	NPD5330	Approved
0.6596	Remote Similarity	NPD6409	Approved
0.6596	Remote Similarity	NPD7146	Approved
0.6596	Remote Similarity	NPD6684	Approved
0.6535	Remote Similarity	NPD4225	Approved
0.6514	Remote Similarity	NPD4632	Approved
0.6512	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6495	Remote Similarity	NPD7136	Phase 2
0.6495	Remote Similarity	NPD4096	Approved
0.6489	Remote Similarity	NPD1696	Phase 3
0.6484	Remote Similarity	NPD4821	Approved
0.6484	Remote Similarity	NPD4822	Approved
0.6484	Remote Similarity	NPD4820	Approved
0.6484	Remote Similarity	NPD4819	Approved
0.6471	Remote Similarity	NPD6404	Discontinued
0.6458	Remote Similarity	NPD6903	Approved
0.6458	Remote Similarity	NPD5737	Approved
0.6458	Remote Similarity	NPD4518	Approved
0.6458	Remote Similarity	NPD6672	Approved
0.6458	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5167	Approved
0.6452	Remote Similarity	NPD5362	Discontinued
0.6452	Remote Similarity	NPD5331	Approved
0.6452	Remote Similarity	NPD5332	Approved
0.6444	Remote Similarity	NPD3617	Approved
0.6436	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD6335	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