NPASS Compound

Structure

NPC275910 OpenBabel07101719122D 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 1.5180 5.8564 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 -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 1.8781 4.1622 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 0.9000 3.9543 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 -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 0.9511 -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 2.1871 5.1132 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 -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 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 11 1 0 0 0 0 9 19 2 0 0 0 0 10 12 1 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 21 1 0 0 0 0 14 18 1 0 0 0 0 14 22 1 0 0 0 0 15 16 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 20 3 1 1 0 0 0 20 21 1 0 0 0 0 20 24 1 0 0 0 0 21 29 1 1 0 0 0 22 23 2 0 0 0 0 22 28 1 0 0 0 0 23 30 1 0 0 0 0 24 31 1 6 0 0 0 25 27 1 0 0 0 0 25 28 1 1 0 0 0 26 27 1 0 0 0 0 26 32 1 1 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:	442.38
Volume:	505.518
LogP:	6.555
LogD:	5.051
LogS:	-5.989
# 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:	0.444
Synthetic Accessibility Score:	4.83
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:	-4.882
MDCK Permeability:	1.1816342521342449e-05
Pgp-inhibitor:	0.841
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.979
30% Bioavailability (F30%):	0.937

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.021
Plasma Protein Binding (PPB):	93.05208587646484%
Volume Distribution (VD):	2.009
Pgp-substrate:	1.560573697090149%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.449
CYP2C19-inhibitor:	0.117
CYP2C19-substrate:	0.959
CYP2C9-inhibitor:	0.236
CYP2C9-substrate:	0.784
CYP2D6-inhibitor:	0.027
CYP2D6-substrate:	0.268
CYP3A4-inhibitor:	0.504
CYP3A4-substrate:	0.66

ADMET: Excretion

Clearance (CL):	7.969
Half-life (T1/2):	0.047

ADMET: Toxicity

hERG Blockers:	0.038
Human Hepatotoxicity (H-HT):	0.268
Drug-inuced Liver Injury (DILI):	0.017
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.188
Maximum Recommended Daily Dose:	0.881
Skin Sensitization:	0.695
Carcinogencity:	0.025
Eye Corrosion:	0.317
Eye Irritation:	0.298
Respiratory Toxicity:	0.699

Download Data

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

Natural Product: NPC275910

Natural Product ID:	NPC275910
*Common Name:**	Inotodiol
IUPAC Name:	(3S,5R,10S,13R,14R,17R)-17-[(2S,3R)-3-hydroxy-6-methylhept-5-en-2-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
Synonyms:	Inotodiol
Standard InCHIKey:	KKWJCGCIAHLFNE-KFPHZHIMSA-N
Standard InCHI:	InChI=1S/C30H50O2/c1-19(2)9-11-24(31)20(3)21-13-17-30(8)23-10-12-25-27(4,5)26(32)15-16-28(25,6)22(23)14-18-29(21,30)7/h9,20-21,24-26,31-32H,10-18H2,1-8H3/t20-,21+,24+,25-,26-,28+,29+,30-/m0/s1
SMILES:	CC(=CC[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)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL449088
PubChem CID:	44422314
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	4
Others	10

Activity Type	# Activity
Cell Line	7
NON-MOLECULAR	1
Organism	5
Others	1

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[486789]
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	171000.0	nM	PMID[486790]
NPT137	Cell Line	L1210	Mus musculus	IC50	=	110000.0	nM	PMID[486790]
NPT168	Cell Line	P388	Mus musculus	Survival	=	20.8	%	PMID[486790]
NPT168	Cell Line	P388	Mus musculus	Survival	=	9.7	%	PMID[486790]
NPT168	Cell Line	P388	Mus musculus	IC50	=	13900.0	nM	PMID[486790]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	25000.0	nM	PMID[486790]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	2.4	%	PMID[486789]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	37.6	%	PMID[486789]
NPT32	Organism	Mus musculus	Mus musculus	Activity	<	30.0	%	PMID[486789]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	66.1	%	PMID[486789]
NPT164	Organism	Human herpesvirus 4	Human herpesvirus 4	Inhibition	=	93.1	%	PMID[486789]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	56.3	%	PMID[486791]
NPT2	Others	Unspecified		Survival	=	86.0	%	PMID[486791]

☑ 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 NPC275910 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	146
0.1-0.2	1299
0.2-0.3	6741
0.3-0.4	16088
0.4-0.5	7517
0.5-0.6	5898
0.6-0.7	3632
0.7-0.8	1052
0.8-0.85	191
0.85-0.9	101
0.9-0.95	23
0.95-1	9

Similarity Score	Similarity Level	Natural Product ID
0.9861	High Similarity	NPC214570
0.9722	High Similarity	NPC202642
0.9722	High Similarity	NPC73875
0.9722	High Similarity	NPC46160
0.9583	High Similarity	NPC121744
0.9583	High Similarity	NPC118508
0.9583	High Similarity	NPC322353
0.9474	High Similarity	NPC201852
0.9459	High Similarity	NPC205455
0.9459	High Similarity	NPC186191
0.9452	High Similarity	NPC321381
0.9452	High Similarity	NPC240604
0.9452	High Similarity	NPC300324
0.9452	High Similarity	NPC321016
0.9452	High Similarity	NPC189883
0.9452	High Similarity	NPC470362
0.9452	High Similarity	NPC107059
0.9342	High Similarity	NPC474531
0.9333	High Similarity	NPC1319
0.9324	High Similarity	NPC198968
0.9324	High Similarity	NPC155986
0.9324	High Similarity	NPC318495
0.9315	High Similarity	NPC134847
0.9315	High Similarity	NPC257347
0.9315	High Similarity	NPC288035
0.9315	High Similarity	NPC141071
0.9315	High Similarity	NPC230301
0.9315	High Similarity	NPC28657
0.9315	High Similarity	NPC471723
0.9315	High Similarity	NPC162742
0.9315	High Similarity	NPC285893
0.9315	High Similarity	NPC22105
0.9315	High Similarity	NPC136188
0.9315	High Similarity	NPC304309
0.9306	High Similarity	NPC201373
0.9221	High Similarity	NPC87489
0.9221	High Similarity	NPC202389
0.9211	High Similarity	NPC236112
0.92	High Similarity	NPC477522
0.92	High Similarity	NPC6978
0.92	High Similarity	NPC167037
0.92	High Similarity	NPC318136
0.92	High Similarity	NPC285761
0.92	High Similarity	NPC474216
0.92	High Similarity	NPC473943
0.92	High Similarity	NPC87604
0.92	High Similarity	NPC138621
0.92	High Similarity	NPC244385
0.9189	High Similarity	NPC129165
0.9189	High Similarity	NPC237460
0.9189	High Similarity	NPC113733
0.9189	High Similarity	NPC134330
0.9091	High Similarity	NPC6707
0.9091	High Similarity	NPC470383
0.9079	High Similarity	NPC28862
0.9079	High Similarity	NPC47982
0.9079	High Similarity	NPC143182
0.9079	High Similarity	NPC84694
0.9079	High Similarity	NPC273410
0.9079	High Similarity	NPC81306
0.9079	High Similarity	NPC30986
0.9079	High Similarity	NPC209430
0.9079	High Similarity	NPC328714
0.9079	High Similarity	NPC80530
0.9079	High Similarity	NPC109546
0.9067	High Similarity	NPC34019
0.9041	High Similarity	NPC474140
0.8987	High Similarity	NPC209802
0.8987	High Similarity	NPC238485
0.8987	High Similarity	NPC231310
0.8987	High Similarity	NPC124172
0.8974	High Similarity	NPC30166
0.8974	High Similarity	NPC101462
0.8974	High Similarity	NPC49964
0.8974	High Similarity	NPC20853
0.8974	High Similarity	NPC470049
0.8974	High Similarity	NPC248886
0.8961	High Similarity	NPC322313
0.8961	High Similarity	NPC13554
0.8961	High Similarity	NPC102253
0.8961	High Similarity	NPC234193
0.8961	High Similarity	NPC236237
0.8961	High Similarity	NPC164840
0.8961	High Similarity	NPC22403
0.8961	High Similarity	NPC209944
0.8961	High Similarity	NPC241290
0.8961	High Similarity	NPC26117
0.8947	High Similarity	NPC302041
0.8947	High Similarity	NPC18603
0.8947	High Similarity	NPC307965
0.8947	High Similarity	NPC85346
0.8947	High Similarity	NPC65897
0.8947	High Similarity	NPC76931
0.8933	High Similarity	NPC96319
0.8919	High Similarity	NPC243342
0.8919	High Similarity	NPC477138
0.8904	High Similarity	NPC110799
0.8861	High Similarity	NPC470384
0.8861	High Similarity	NPC317458
0.8846	High Similarity	NPC47761
0.8846	High Similarity	NPC474752
0.8846	High Similarity	NPC209620
0.8846	High Similarity	NPC474683
0.8846	High Similarity	NPC474759
0.8846	High Similarity	NPC23852
0.8846	High Similarity	NPC82986
0.8846	High Similarity	NPC474731
0.8846	High Similarity	NPC264245
0.8846	High Similarity	NPC7505
0.8831	High Similarity	NPC472463
0.8816	High Similarity	NPC471798
0.88	High Similarity	NPC471468
0.88	High Similarity	NPC291503
0.88	High Similarity	NPC477923
0.88	High Similarity	NPC66566
0.8784	High Similarity	NPC182717
0.8784	High Similarity	NPC471799
0.878	High Similarity	NPC471722
0.878	High Similarity	NPC470542
0.8767	High Similarity	NPC92801
0.8765	High Similarity	NPC474970
0.8765	High Similarity	NPC24277
0.8765	High Similarity	NPC261266
0.8765	High Similarity	NPC6391
0.8765	High Similarity	NPC94755
0.8765	High Similarity	NPC94462
0.875	High Similarity	NPC478102
0.875	High Similarity	NPC205845
0.875	High Similarity	NPC185568
0.875	High Similarity	NPC208999
0.875	High Similarity	NPC470077
0.8734	High Similarity	NPC189972
0.8734	High Similarity	NPC470614
0.8734	High Similarity	NPC218616
0.8734	High Similarity	NPC1272
0.8734	High Similarity	NPC7988
0.8734	High Similarity	NPC5985
0.8734	High Similarity	NPC296701
0.8734	High Similarity	NPC50964
0.8701	High Similarity	NPC22955
0.8701	High Similarity	NPC470396
0.8701	High Similarity	NPC312328
0.8701	High Similarity	NPC474989
0.8701	High Similarity	NPC477514
0.8701	High Similarity	NPC99168
0.8684	High Similarity	NPC247325
0.8684	High Similarity	NPC244488
0.8684	High Similarity	NPC265588
0.8667	High Similarity	NPC100334
0.8667	High Similarity	NPC469534
0.8667	High Similarity	NPC91858
0.8667	High Similarity	NPC469533
0.8667	High Similarity	NPC471797
0.8667	High Similarity	NPC469593
0.8659	High Similarity	NPC187376
0.8659	High Similarity	NPC475772
0.8659	High Similarity	NPC159046
0.8659	High Similarity	NPC233836
0.8659	High Similarity	NPC271967
0.8649	High Similarity	NPC242001
0.8649	High Similarity	NPC167706
0.8649	High Similarity	NPC111234
0.8642	High Similarity	NPC266511
0.8642	High Similarity	NPC274448
0.8642	High Similarity	NPC157257
0.8642	High Similarity	NPC318390
0.8625	High Similarity	NPC475789
0.8625	High Similarity	NPC474634
0.8625	High Similarity	NPC113978
0.8625	High Similarity	NPC207013
0.8625	High Similarity	NPC477818
0.8625	High Similarity	NPC110778
0.859	High Similarity	NPC53744
0.859	High Similarity	NPC291379
0.8571	High Similarity	NPC192437
0.8571	High Similarity	NPC91594
0.8571	High Similarity	NPC477924
0.8571	High Similarity	NPC472805
0.8571	High Similarity	NPC101475
0.8571	High Similarity	NPC157996
0.8571	High Similarity	NPC90979
0.8571	High Similarity	NPC40394
0.8571	High Similarity	NPC34177
0.8571	High Similarity	NPC245410
0.8571	High Similarity	NPC470390
0.8571	High Similarity	NPC270511
0.8554	High Similarity	NPC2158
0.8554	High Similarity	NPC242864
0.8553	High Similarity	NPC70982
0.8553	High Similarity	NPC212879
0.8553	High Similarity	NPC3403
0.8553	High Similarity	NPC104387
0.8553	High Similarity	NPC240235
0.8553	High Similarity	NPC231256
0.8553	High Similarity	NPC185536
0.8553	High Similarity	NPC230704
0.8553	High Similarity	NPC178383
0.8537	High Similarity	NPC55309
0.8537	High Similarity	NPC477604
0.8537	High Similarity	NPC72133

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 NPC275910 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	137
0.1-0.2	1670
0.2-0.3	4408
0.3-0.4	2081
0.4-0.5	437
0.5-0.6	178
0.6-0.7	171
0.7-0.8	53
0.8-0.85	12
0.85-0.9	3
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9315	High Similarity	NPD6942	Approved
0.9315	High Similarity	NPD7339	Approved
0.8961	High Similarity	NPD7525	Registered
0.8933	High Similarity	NPD3701	Clinical (unspecified phase)
0.8519	High Similarity	NPD4786	Approved
0.8481	Intermediate Similarity	NPD4748	Discontinued
0.8421	Intermediate Similarity	NPD6926	Approved
0.8421	Intermediate Similarity	NPD6924	Approved
0.8354	Intermediate Similarity	NPD7645	Phase 2
0.8272	Intermediate Similarity	NPD3667	Approved
0.8235	Intermediate Similarity	NPD5328	Approved
0.8205	Intermediate Similarity	NPD6933	Approved
0.8182	Intermediate Similarity	NPD4785	Approved
0.8182	Intermediate Similarity	NPD4784	Approved
0.8158	Intermediate Similarity	NPD4243	Approved
0.8158	Intermediate Similarity	NPD7151	Approved
0.8158	Intermediate Similarity	NPD7150	Approved
0.8158	Intermediate Similarity	NPD7152	Approved
0.8133	Intermediate Similarity	NPD6922	Approved
0.8133	Intermediate Similarity	NPD6923	Approved
0.8095	Intermediate Similarity	NPD3618	Phase 1
0.8046	Intermediate Similarity	NPD6079	Approved
0.8026	Intermediate Similarity	NPD7144	Approved
0.8026	Intermediate Similarity	NPD7143	Approved
0.8	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6929	Approved
0.7848	Intermediate Similarity	NPD8264	Approved
0.7805	Intermediate Similarity	NPD6931	Approved
0.7805	Intermediate Similarity	NPD6930	Phase 2
0.7805	Intermediate Similarity	NPD7509	Discontinued
0.7753	Intermediate Similarity	NPD4202	Approved
0.7674	Intermediate Similarity	NPD5279	Phase 3
0.7654	Intermediate Similarity	NPD6932	Approved
0.7654	Intermediate Similarity	NPD5776	Phase 2
0.7654	Intermediate Similarity	NPD6925	Approved
0.7647	Intermediate Similarity	NPD3133	Approved
0.7647	Intermediate Similarity	NPD3666	Approved
0.7647	Intermediate Similarity	NPD3665	Phase 1
0.7625	Intermediate Similarity	NPD5275	Approved
0.7625	Intermediate Similarity	NPD4190	Phase 3
0.7561	Intermediate Similarity	NPD7145	Approved
0.7558	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6399	Phase 3
0.7529	Intermediate Similarity	NPD6695	Phase 3
0.75	Intermediate Similarity	NPD5222	Approved
0.75	Intermediate Similarity	NPD4697	Phase 3
0.75	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5221	Approved
0.747	Intermediate Similarity	NPD4195	Approved
0.747	Intermediate Similarity	NPD6683	Phase 2
0.7442	Intermediate Similarity	NPD3668	Phase 3
0.7442	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD4755	Approved
0.7419	Intermediate Similarity	NPD5173	Approved
0.7381	Intermediate Similarity	NPD7514	Phase 3
0.7356	Intermediate Similarity	NPD6893	Approved
0.7349	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD6902	Approved
0.7263	Intermediate Similarity	NPD4700	Approved
0.7263	Intermediate Similarity	NPD4696	Approved
0.7263	Intermediate Similarity	NPD5286	Approved
0.7263	Intermediate Similarity	NPD5285	Approved
0.7253	Intermediate Similarity	NPD7515	Phase 2
0.7222	Intermediate Similarity	NPD4753	Phase 2
0.7215	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD4221	Approved
0.7209	Intermediate Similarity	NPD4223	Phase 3
0.7191	Intermediate Similarity	NPD7524	Approved
0.7191	Intermediate Similarity	NPD7750	Discontinued
0.7188	Intermediate Similarity	NPD5223	Approved
0.7176	Intermediate Similarity	NPD7332	Phase 2
0.7159	Intermediate Similarity	NPD5329	Approved
0.7158	Intermediate Similarity	NPD5290	Discontinued
0.7158	Intermediate Similarity	NPD7638	Approved
0.7113	Intermediate Similarity	NPD5225	Approved
0.7113	Intermediate Similarity	NPD4633	Approved
0.7113	Intermediate Similarity	NPD5224	Approved
0.7113	Intermediate Similarity	NPD5211	Phase 2
0.7113	Intermediate Similarity	NPD5226	Approved
0.7093	Intermediate Similarity	NPD6898	Phase 1
0.7083	Intermediate Similarity	NPD7639	Approved
0.7083	Intermediate Similarity	NPD7640	Approved
0.7079	Intermediate Similarity	NPD5690	Phase 2
0.7079	Intermediate Similarity	NPD5280	Approved
0.7079	Intermediate Similarity	NPD4694	Approved
0.7071	Intermediate Similarity	NPD6675	Approved
0.7071	Intermediate Similarity	NPD6402	Approved
0.7071	Intermediate Similarity	NPD7128	Approved
0.7071	Intermediate Similarity	NPD5739	Approved
0.7045	Intermediate Similarity	NPD4197	Approved
0.7041	Intermediate Similarity	NPD5175	Approved
0.7041	Intermediate Similarity	NPD5174	Approved
0.7041	Intermediate Similarity	NPD4754	Approved
0.697	Remote Similarity	NPD5141	Approved
0.6932	Remote Similarity	NPD4788	Approved
0.6931	Remote Similarity	NPD6899	Approved
0.6931	Remote Similarity	NPD7320	Approved
0.6931	Remote Similarity	NPD6881	Approved
0.6915	Remote Similarity	NPD7748	Approved
0.6914	Remote Similarity	NPD4787	Phase 1
0.69	Remote Similarity	NPD4767	Approved
0.69	Remote Similarity	NPD4768	Approved
0.6897	Remote Similarity	NPD4692	Approved
0.6897	Remote Similarity	NPD4139	Approved
0.6889	Remote Similarity	NPD6684	Approved
0.6889	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD4689	Approved
0.6889	Remote Similarity	NPD4693	Phase 3
0.6889	Remote Similarity	NPD5330	Approved
0.6889	Remote Similarity	NPD7521	Approved
0.6889	Remote Similarity	NPD7146	Approved
0.6889	Remote Similarity	NPD4688	Approved
0.6889	Remote Similarity	NPD6409	Approved
0.6889	Remote Similarity	NPD4138	Approved
0.6889	Remote Similarity	NPD7334	Approved
0.6889	Remote Similarity	NPD5205	Approved
0.6889	Remote Similarity	NPD4690	Approved
0.6882	Remote Similarity	NPD8035	Phase 2
0.6882	Remote Similarity	NPD8034	Phase 2
0.6882	Remote Similarity	NPD7087	Discontinued
0.6875	Remote Similarity	NPD6084	Phase 2
0.6875	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6373	Approved
0.6863	Remote Similarity	NPD6372	Approved
0.6848	Remote Similarity	NPD6051	Approved
0.6842	Remote Similarity	NPD4629	Approved
0.6842	Remote Similarity	NPD5210	Approved
0.6842	Remote Similarity	NPD5695	Phase 3
0.6832	Remote Similarity	NPD5701	Approved
0.6832	Remote Similarity	NPD5697	Approved
0.6829	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6829	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD6883	Approved
0.6796	Remote Similarity	NPD7290	Approved
0.6796	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD4730	Approved
0.6765	Remote Similarity	NPD6011	Approved
0.6765	Remote Similarity	NPD5168	Approved
0.6765	Remote Similarity	NPD4729	Approved
0.6765	Remote Similarity	NPD5128	Approved
0.6753	Remote Similarity	NPD368	Approved
0.6744	Remote Similarity	NPD3617	Approved
0.6739	Remote Similarity	NPD5737	Approved
0.6739	Remote Similarity	NPD6903	Approved
0.6739	Remote Similarity	NPD4722	Approved
0.6739	Remote Similarity	NPD4723	Approved
0.6739	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD6672	Approved
0.6731	Remote Similarity	NPD6650	Approved
0.6731	Remote Similarity	NPD8130	Phase 1
0.6731	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD6617	Approved
0.6731	Remote Similarity	NPD6649	Approved
0.6731	Remote Similarity	NPD6869	Approved
0.6731	Remote Similarity	NPD6847	Approved
0.6706	Remote Similarity	NPD6117	Approved
0.6702	Remote Similarity	NPD6411	Approved
0.6702	Remote Similarity	NPD5284	Approved
0.6702	Remote Similarity	NPD5281	Approved
0.6701	Remote Similarity	NPD7902	Approved
0.6699	Remote Similarity	NPD6013	Approved
0.6699	Remote Similarity	NPD6014	Approved
0.6699	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5733	Approved
0.6667	Remote Similarity	NPD8297	Approved
0.6667	Remote Similarity	NPD6882	Approved
0.6667	Remote Similarity	NPD4159	Approved
0.6667	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD5135	Approved
0.6635	Remote Similarity	NPD5250	Approved
0.6635	Remote Similarity	NPD5248	Approved
0.6635	Remote Similarity	NPD5169	Approved
0.6635	Remote Similarity	NPD5249	Phase 3
0.6635	Remote Similarity	NPD5247	Approved
0.6635	Remote Similarity	NPD5251	Approved
0.6635	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD4634	Approved
0.6628	Remote Similarity	NPD6116	Phase 1
0.6596	Remote Similarity	NPD4096	Approved
0.6591	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4695	Discontinued
0.6585	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7115	Discovery
0.6571	Remote Similarity	NPD5217	Approved
0.6571	Remote Similarity	NPD5215	Approved
0.6571	Remote Similarity	NPD5216	Approved
0.6571	Remote Similarity	NPD5127	Approved
0.6559	Remote Similarity	NPD4518	Approved
0.6552	Remote Similarity	NPD6115	Approved
0.6552	Remote Similarity	NPD6114	Approved
0.6552	Remote Similarity	NPD6697	Approved
0.6552	Remote Similarity	NPD6118	Approved
0.6526	Remote Similarity	NPD7637	Suspended
0.6522	Remote Similarity	NPD6098	Approved
0.6506	Remote Similarity	NPD4747	Approved
0.6495	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD6101	Approved
0.6489	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6481	Remote Similarity	NPD6868	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