NPASS Compound

Structure

CID73875 OpenBabel06191715412D 33 36 0 0 1 0 0 0 0 0999 V2000 -0.0789 -6.5794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4621 -5.8928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8717 -4.8001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3779 2.9594 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2526 2.4542 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5331 -0.5236 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0006 -1.9848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0003 1.0104 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6692 -4.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2728 -3.2238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8448 1.4622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6894 1.9495 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6879 -0.9739 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6885 -0.9749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2210 0.4863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3770 -0.0010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6876 0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8440 -1.4621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8138 -2.5372 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4934 -5.7913 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0970 -4.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8451 -2.4357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8448 -1.4617 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.6888 -0.0005 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8445 0.4873 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5336 1.4618 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.2212 1.4613 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.3776 1.9490 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5333 0.4868 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0003 -0.9744 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 2.2102 -3.4269 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0874 1.9610 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 21 2 0 0 0 0 4 28 1 0 0 0 0 5 28 1 0 0 0 0 7 30 1 0 0 0 0 9 10 1 0 0 0 0 9 21 1 0 0 0 0 11 12 1 0 0 0 0 11 25 1 0 0 0 0 12 26 1 0 0 0 0 13 17 1 0 0 0 0 13 23 1 0 0 0 0 14 18 1 0 0 0 0 14 24 1 0 0 0 0 15 16 1 0 0 0 0 15 27 1 0 0 0 0 16 29 1 0 0 0 0 17 31 1 0 0 0 0 18 30 1 0 0 0 0 19 22 1 0 0 0 0 19 32 1 0 0 0 0 20 21 1 0 0 0 0 22 10 1 6 0 0 0 22 23 1 0 0 0 0 23 30 1 6 0 0 0 24 25 2 0 0 0 0 24 29 1 0 0 0 0 25 31 1 0 0 0 0 26 28 1 0 0 0 0 26 29 1 6 0 0 0 27 28 1 0 0 0 0 27 33 1 6 0 0 0 29 6 1 6 0 0 0 30 31 1 6 0 0 0 31 8 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	456.4
Volume:	522.814
LogP:	6.346
LogD:	5.147
LogS:	-5.859
# Rotatable Bonds:	6
TPSA:	40.46
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.402
Synthetic Accessibility Score:	4.829
Fsp3:	0.871
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:	-4.904
MDCK Permeability:	9.870442227111198e-06
Pgp-inhibitor:	0.918
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.911
30% Bioavailability (F30%):	0.444

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.028
Plasma Protein Binding (PPB):	93.5569839477539%
Volume Distribution (VD):	1.092
Pgp-substrate:	1.458363652229309%

ADMET: Metabolism

CYP1A2-inhibitor:	0.024
CYP1A2-substrate:	0.62
CYP2C19-inhibitor:	0.073
CYP2C19-substrate:	0.972
CYP2C9-inhibitor:	0.16
CYP2C9-substrate:	0.553
CYP2D6-inhibitor:	0.028
CYP2D6-substrate:	0.852
CYP3A4-inhibitor:	0.551
CYP3A4-substrate:	0.848

ADMET: Excretion

Clearance (CL):	7.014
Half-life (T1/2):	0.05

ADMET: Toxicity

hERG Blockers:	0.018
Human Hepatotoxicity (H-HT):	0.062
Drug-inuced Liver Injury (DILI):	0.035
AMES Toxicity:	0.007
Rat Oral Acute Toxicity:	0.154
Maximum Recommended Daily Dose:	0.903
Skin Sensitization:	0.149
Carcinogencity:	0.018
Eye Corrosion:	0.061
Eye Irritation:	0.455
Respiratory Toxicity:	0.491

Download Data

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

Natural Product: NPC73875

Natural Product ID:	NPC73875
*Common Name:**	Dehydroeburicol[(20R)-24-Methyllanosta-7,9(11),24-(24')-Triene-3Beta,21-Diol]
IUPAC Name:	(3S,5R,10S,13R,14R,17R)-17-[(2R)-1-hydroxy-6-methyl-5-methylideneheptan-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:
Standard InCHIKey:	GDLCVKONYVOCKC-ITKMBEFXSA-N
Standard InCHI:	InChI=1S/C31H52O2/c1-20(2)21(3)9-10-22(19-32)23-13-17-31(8)25-11-12-26-28(4,5)27(33)15-16-29(26,6)24(25)14-18-30(23,31)7/h20,22-23,26-27,32-33H,3,9-19H2,1-2,4-8H3/t22-,23+,26-,27-,29+,30+,31-/m0/s1
SMILES:	CC(C)C(=C)CC[C@@H](CO)[C@H]1CC[C@@]2(C)C3=C(CC[C@]12C)[C@@]1(C)CC[C@@H](C(C)(C)[C@@H]1CC3)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1765431
PubChem CID:	51039599
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
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3354	Fomes officinalis	Species	Coriolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3354	Fomes officinalis	Species	Coriolaceae	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	8

Activity Type	# Activity
Cell Line	6
NON-MOLECULAR	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT81	Cell Line	A549	Homo sapiens	IC50	=	4000.0	nM	PMID[468563]
NPT377	Cell Line	OVCAR-3	Homo sapiens	IC50	=	6400.0	nM	PMID[468563]
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	6700.0	nM	PMID[468563]
NPT134	Cell Line	SK-BR-3	Homo sapiens	IC50	=	11700.0	nM	PMID[468563]
NPT461	Cell Line	PANC-1	Homo sapiens	IC50	=	22600.0	nM	PMID[468563]
NPT90	Cell Line	DU-145	Homo sapiens	IC50	=	100000.0	nM	PMID[468563]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2800.0	nM	PMID[468563]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	12500.0	nM	PMID[468563]

☑ 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 NPC73875 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	142
0.1-0.2	1455
0.2-0.3	8377
0.3-0.4	15620
0.4-0.5	6579
0.5-0.6	5949
0.6-0.7	3304
0.7-0.8	1004
0.8-0.85	172
0.85-0.9	68
0.9-0.95	15
0.95-1	12

Similarity Score	Similarity Level	Natural Product ID
0.9859	High Similarity	NPC214570
0.9857	High Similarity	NPC118508
0.9857	High Similarity	NPC322353
0.9857	High Similarity	NPC121744
0.9722	High Similarity	NPC275910
0.9718	High Similarity	NPC46160
0.9718	High Similarity	NPC202642
0.9571	High Similarity	NPC201373
0.9452	High Similarity	NPC205455
0.9452	High Similarity	NPC186191
0.9444	High Similarity	NPC189883
0.9444	High Similarity	NPC470362
0.9324	High Similarity	NPC1319
0.9306	High Similarity	NPC471723
0.9306	High Similarity	NPC257347
0.9306	High Similarity	NPC141071
0.9211	High Similarity	NPC87489
0.9211	High Similarity	NPC202389
0.9211	High Similarity	NPC201852
0.92	High Similarity	NPC236112
0.9189	High Similarity	NPC285761
0.9189	High Similarity	NPC167037
0.9189	High Similarity	NPC138621
0.9189	High Similarity	NPC318136
0.9189	High Similarity	NPC244385
0.9189	High Similarity	NPC6978
0.9178	High Similarity	NPC321016
0.9178	High Similarity	NPC240604
0.9178	High Similarity	NPC134330
0.9178	High Similarity	NPC107059
0.9178	High Similarity	NPC129165
0.9178	High Similarity	NPC321381
0.9178	High Similarity	NPC300324
0.9178	High Similarity	NPC237460
0.9079	High Similarity	NPC474531
0.9079	High Similarity	NPC6707
0.9067	High Similarity	NPC273410
0.9067	High Similarity	NPC30986
0.9067	High Similarity	NPC209430
0.9067	High Similarity	NPC80530
0.9054	High Similarity	NPC198968
0.9054	High Similarity	NPC318495
0.9054	High Similarity	NPC155986
0.9041	High Similarity	NPC28657
0.9041	High Similarity	NPC288035
0.9041	High Similarity	NPC162742
0.9041	High Similarity	NPC136188
0.9041	High Similarity	NPC134847
0.9041	High Similarity	NPC285893
0.9041	High Similarity	NPC22105
0.9041	High Similarity	NPC230301
0.9041	High Similarity	NPC304309
0.9028	High Similarity	NPC474140
0.8974	High Similarity	NPC231310
0.8961	High Similarity	NPC470049
0.8961	High Similarity	NPC30166
0.8961	High Similarity	NPC20853
0.8947	High Similarity	NPC13554
0.8947	High Similarity	NPC322313
0.8947	High Similarity	NPC102253
0.8947	High Similarity	NPC22403
0.8947	High Similarity	NPC236237
0.8933	High Similarity	NPC87604
0.8933	High Similarity	NPC65897
0.8933	High Similarity	NPC477522
0.8933	High Similarity	NPC474216
0.8933	High Similarity	NPC473943
0.8933	High Similarity	NPC302041
0.8933	High Similarity	NPC85346
0.8919	High Similarity	NPC113733
0.8904	High Similarity	NPC469593
0.8904	High Similarity	NPC469533
0.8904	High Similarity	NPC469534
0.8889	High Similarity	NPC110799
0.8889	High Similarity	NPC111234
0.8831	High Similarity	NPC470383
0.8816	High Similarity	NPC109546
0.8816	High Similarity	NPC81306
0.8816	High Similarity	NPC84694
0.8816	High Similarity	NPC143182
0.8816	High Similarity	NPC328714
0.8816	High Similarity	NPC28862
0.8816	High Similarity	NPC47982
0.88	High Similarity	NPC34019
0.8784	High Similarity	NPC231256
0.8784	High Similarity	NPC240235
0.8784	High Similarity	NPC185536
0.8784	High Similarity	NPC230704
0.8784	High Similarity	NPC70982
0.8784	High Similarity	NPC104387
0.8784	High Similarity	NPC3403
0.8784	High Similarity	NPC178383
0.8784	High Similarity	NPC212879
0.8767	High Similarity	NPC182717
0.875	High Similarity	NPC94755
0.875	High Similarity	NPC45296
0.875	High Similarity	NPC72133
0.875	High Similarity	NPC28252
0.875	High Similarity	NPC55309
0.8734	High Similarity	NPC124172
0.8734	High Similarity	NPC238485
0.8734	High Similarity	NPC209802
0.8734	High Similarity	NPC478102
0.8734	High Similarity	NPC470077
0.8718	High Similarity	NPC218616
0.8718	High Similarity	NPC7988
0.8718	High Similarity	NPC296701
0.8718	High Similarity	NPC49964
0.8718	High Similarity	NPC101462
0.8718	High Similarity	NPC248886
0.8701	High Similarity	NPC241290
0.8701	High Similarity	NPC209944
0.8701	High Similarity	NPC234193
0.8701	High Similarity	NPC26117
0.8701	High Similarity	NPC164840
0.8684	High Similarity	NPC312328
0.8684	High Similarity	NPC76931
0.8684	High Similarity	NPC18603
0.8684	High Similarity	NPC477514
0.8684	High Similarity	NPC307965
0.8667	High Similarity	NPC247325
0.8667	High Similarity	NPC91573
0.8667	High Similarity	NPC78067
0.8667	High Similarity	NPC278091
0.8667	High Similarity	NPC244488
0.8667	High Similarity	NPC14112
0.8667	High Similarity	NPC96319
0.8667	High Similarity	NPC93662
0.8667	High Similarity	NPC86305
0.8649	High Similarity	NPC145552
0.8649	High Similarity	NPC254509
0.8649	High Similarity	NPC243342
0.8649	High Similarity	NPC196358
0.8649	High Similarity	NPC477138
0.8649	High Similarity	NPC308440
0.8649	High Similarity	NPC472503
0.8649	High Similarity	NPC100334
0.8649	High Similarity	NPC192638
0.8649	High Similarity	NPC25511
0.8649	High Similarity	NPC91858
0.8649	High Similarity	NPC49168
0.8649	High Similarity	NPC62657
0.8649	High Similarity	NPC5046
0.8642	High Similarity	NPC233836
0.8642	High Similarity	NPC187376
0.8642	High Similarity	NPC159046
0.8642	High Similarity	NPC475772
0.863	High Similarity	NPC167706
0.8625	High Similarity	NPC318390
0.8608	High Similarity	NPC113978
0.8608	High Similarity	NPC477818
0.8608	High Similarity	NPC470384
0.8608	High Similarity	NPC207013
0.8608	High Similarity	NPC132635
0.8608	High Similarity	NPC110778
0.8608	High Similarity	NPC317458
0.859	High Similarity	NPC474752
0.859	High Similarity	NPC82986
0.859	High Similarity	NPC474759
0.859	High Similarity	NPC474731
0.859	High Similarity	NPC474683
0.859	High Similarity	NPC264245
0.859	High Similarity	NPC47761
0.859	High Similarity	NPC7505
0.859	High Similarity	NPC23852
0.859	High Similarity	NPC209620
0.8571	High Similarity	NPC472463
0.8553	High Similarity	NPC34177
0.8553	High Similarity	NPC248830
0.8553	High Similarity	NPC471798
0.8553	High Similarity	NPC472805
0.8553	High Similarity	NPC101475
0.8553	High Similarity	NPC202540
0.8553	High Similarity	NPC331618
0.8553	High Similarity	NPC157996
0.8553	High Similarity	NPC90979
0.8553	High Similarity	NPC40394
0.8553	High Similarity	NPC257191
0.8553	High Similarity	NPC119355
0.8553	High Similarity	NPC212241
0.8537	High Similarity	NPC471722
0.8537	High Similarity	NPC470542
0.8537	High Similarity	NPC143767
0.8537	High Similarity	NPC131470
0.8537	High Similarity	NPC471724
0.8537	High Similarity	NPC242864
0.8533	High Similarity	NPC291503
0.8533	High Similarity	NPC66566
0.8533	High Similarity	NPC471468
0.8533	High Similarity	NPC200243
0.8533	High Similarity	NPC477923
0.8519	High Similarity	NPC261266
0.8519	High Similarity	NPC94462
0.8519	High Similarity	NPC125399
0.8519	High Similarity	NPC24277
0.8519	High Similarity	NPC6391
0.8519	High Similarity	NPC474970
0.8514	High Similarity	NPC195489
0.8514	High Similarity	NPC471799
0.85	High Similarity	NPC185568

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 NPC73875 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	132
0.1-0.2	1864
0.2-0.3	4500
0.3-0.4	1926
0.4-0.5	331
0.5-0.6	162
0.6-0.7	169
0.7-0.8	59
0.8-0.85	5
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9041	High Similarity	NPD6942	Approved
0.9041	High Similarity	NPD7339	Approved
0.8947	High Similarity	NPD7525	Registered
0.8667	High Similarity	NPD3701	Clinical (unspecified phase)
0.8462	Intermediate Similarity	NPD4748	Discontinued
0.8333	Intermediate Similarity	NPD7645	Phase 2
0.8272	Intermediate Similarity	NPD4786	Approved
0.8214	Intermediate Similarity	NPD5328	Approved
0.8158	Intermediate Similarity	NPD6926	Approved
0.8158	Intermediate Similarity	NPD6924	Approved
0.8133	Intermediate Similarity	NPD4243	Approved
0.8072	Intermediate Similarity	NPD3618	Phase 1
0.8025	Intermediate Similarity	NPD3667	Approved
0.8023	Intermediate Similarity	NPD6079	Approved
0.7949	Intermediate Similarity	NPD6933	Approved
0.7922	Intermediate Similarity	NPD4785	Approved
0.7922	Intermediate Similarity	NPD4784	Approved
0.7895	Intermediate Similarity	NPD7151	Approved
0.7895	Intermediate Similarity	NPD7150	Approved
0.7895	Intermediate Similarity	NPD7152	Approved
0.7867	Intermediate Similarity	NPD6923	Approved
0.7867	Intermediate Similarity	NPD6922	Approved
0.7765	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7144	Approved
0.7763	Intermediate Similarity	NPD7143	Approved
0.7738	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4202	Approved
0.7654	Intermediate Similarity	NPD6929	Approved
0.7647	Intermediate Similarity	NPD5279	Phase 3
0.7619	Intermediate Similarity	NPD3133	Approved
0.7619	Intermediate Similarity	NPD3666	Approved
0.7619	Intermediate Similarity	NPD3665	Phase 1
0.7595	Intermediate Similarity	NPD4190	Phase 3
0.7595	Intermediate Similarity	NPD8264	Approved
0.7595	Intermediate Similarity	NPD5275	Approved
0.7561	Intermediate Similarity	NPD7509	Discontinued
0.7561	Intermediate Similarity	NPD6931	Approved
0.7561	Intermediate Similarity	NPD6930	Phase 2
0.7473	Intermediate Similarity	NPD5221	Approved
0.7473	Intermediate Similarity	NPD5222	Approved
0.7473	Intermediate Similarity	NPD4697	Phase 3
0.7473	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD4195	Approved
0.7407	Intermediate Similarity	NPD5776	Phase 2
0.7407	Intermediate Similarity	NPD6932	Approved
0.7407	Intermediate Similarity	NPD6925	Approved
0.7403	Intermediate Similarity	NPD4267	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD4755	Approved
0.7391	Intermediate Similarity	NPD5173	Approved
0.7333	Intermediate Similarity	NPD6399	Phase 3
0.7317	Intermediate Similarity	NPD7145	Approved
0.7294	Intermediate Similarity	NPD6695	Phase 3
0.7234	Intermediate Similarity	NPD4696	Approved
0.7234	Intermediate Similarity	NPD5285	Approved
0.7234	Intermediate Similarity	NPD5286	Approved
0.7234	Intermediate Similarity	NPD4700	Approved
0.7229	Intermediate Similarity	NPD6683	Phase 2
0.7222	Intermediate Similarity	NPD7515	Phase 2
0.7209	Intermediate Similarity	NPD3668	Phase 3
0.7209	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD4753	Phase 2
0.7176	Intermediate Similarity	NPD4221	Approved
0.7176	Intermediate Similarity	NPD4223	Phase 3
0.7158	Intermediate Similarity	NPD5223	Approved
0.7143	Intermediate Similarity	NPD7514	Phase 3
0.7128	Intermediate Similarity	NPD7638	Approved
0.7128	Intermediate Similarity	NPD5290	Discontinued
0.7126	Intermediate Similarity	NPD5329	Approved
0.7126	Intermediate Similarity	NPD6893	Approved
0.7108	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD4788	Approved
0.7089	Intermediate Similarity	NPD4787	Phase 1
0.7083	Intermediate Similarity	NPD5226	Approved
0.7083	Intermediate Similarity	NPD5211	Phase 2
0.7083	Intermediate Similarity	NPD5224	Approved
0.7083	Intermediate Similarity	NPD4633	Approved
0.7083	Intermediate Similarity	NPD5225	Approved
0.7059	Intermediate Similarity	NPD6902	Approved
0.7059	Intermediate Similarity	NPD4692	Approved
0.7059	Intermediate Similarity	NPD4139	Approved
0.7053	Intermediate Similarity	NPD7640	Approved
0.7053	Intermediate Similarity	NPD7639	Approved
0.7045	Intermediate Similarity	NPD5280	Approved
0.7045	Intermediate Similarity	NPD4694	Approved
0.7045	Intermediate Similarity	NPD5690	Phase 2
0.7041	Intermediate Similarity	NPD6675	Approved
0.7041	Intermediate Similarity	NPD6402	Approved
0.7041	Intermediate Similarity	NPD7128	Approved
0.7041	Intermediate Similarity	NPD5739	Approved
0.7033	Intermediate Similarity	NPD8035	Phase 2
0.7033	Intermediate Similarity	NPD8034	Phase 2
0.7011	Intermediate Similarity	NPD4197	Approved
0.701	Intermediate Similarity	NPD5174	Approved
0.701	Intermediate Similarity	NPD5175	Approved
0.701	Intermediate Similarity	NPD4754	Approved
0.7	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.6966	Remote Similarity	NPD7750	Discontinued
0.6966	Remote Similarity	NPD7524	Approved
0.6941	Remote Similarity	NPD7332	Phase 2
0.6939	Remote Similarity	NPD5141	Approved
0.6905	Remote Similarity	NPD3617	Approved
0.69	Remote Similarity	NPD7320	Approved
0.69	Remote Similarity	NPD6881	Approved
0.69	Remote Similarity	NPD6899	Approved
0.6882	Remote Similarity	NPD7748	Approved
0.6869	Remote Similarity	NPD4767	Approved
0.6869	Remote Similarity	NPD4768	Approved
0.6867	Remote Similarity	NPD6117	Approved
0.686	Remote Similarity	NPD6898	Phase 1
0.6854	Remote Similarity	NPD7334	Approved
0.6854	Remote Similarity	NPD4688	Approved
0.6854	Remote Similarity	NPD6409	Approved
0.6854	Remote Similarity	NPD5330	Approved
0.6854	Remote Similarity	NPD7146	Approved
0.6854	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6854	Remote Similarity	NPD4693	Phase 3
0.6854	Remote Similarity	NPD7521	Approved
0.6854	Remote Similarity	NPD4689	Approved
0.6854	Remote Similarity	NPD5205	Approved
0.6854	Remote Similarity	NPD4138	Approved
0.6854	Remote Similarity	NPD4690	Approved
0.6854	Remote Similarity	NPD6684	Approved
0.6842	Remote Similarity	NPD6083	Phase 2
0.6842	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD6373	Approved
0.6832	Remote Similarity	NPD6372	Approved
0.6829	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6051	Approved
0.6809	Remote Similarity	NPD5695	Phase 3
0.6809	Remote Similarity	NPD4629	Approved
0.6809	Remote Similarity	NPD5210	Approved
0.68	Remote Similarity	NPD5697	Approved
0.68	Remote Similarity	NPD5701	Approved
0.6786	Remote Similarity	NPD6116	Phase 1
0.6765	Remote Similarity	NPD7102	Approved
0.6765	Remote Similarity	NPD6883	Approved
0.6765	Remote Similarity	NPD7290	Approved
0.675	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.675	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5128	Approved
0.6733	Remote Similarity	NPD4730	Approved
0.6733	Remote Similarity	NPD6011	Approved
0.6733	Remote Similarity	NPD5168	Approved
0.6733	Remote Similarity	NPD4729	Approved
0.6711	Remote Similarity	NPD368	Approved
0.6706	Remote Similarity	NPD6118	Approved
0.6706	Remote Similarity	NPD6114	Approved
0.6706	Remote Similarity	NPD6115	Approved
0.6706	Remote Similarity	NPD6697	Approved
0.6703	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD4723	Approved
0.6703	Remote Similarity	NPD5737	Approved
0.6703	Remote Similarity	NPD6903	Approved
0.6703	Remote Similarity	NPD4722	Approved
0.6703	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD6847	Approved
0.6699	Remote Similarity	NPD6649	Approved
0.6699	Remote Similarity	NPD6650	Approved
0.6699	Remote Similarity	NPD6617	Approved
0.6699	Remote Similarity	NPD6869	Approved
0.6699	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD8130	Phase 1
0.6667	Remote Similarity	NPD6014	Approved
0.6667	Remote Similarity	NPD6012	Approved
0.6667	Remote Similarity	NPD5284	Approved
0.6667	Remote Similarity	NPD6013	Approved
0.6667	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD5281	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6635	Remote Similarity	NPD6882	Approved
0.6635	Remote Similarity	NPD8297	Approved
0.6633	Remote Similarity	NPD4159	Approved
0.6627	Remote Similarity	NPD5733	Approved
0.6602	Remote Similarity	NPD5251	Approved
0.6602	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5250	Approved
0.6602	Remote Similarity	NPD5247	Approved
0.6602	Remote Similarity	NPD5248	Approved
0.6602	Remote Similarity	NPD5169	Approved
0.6602	Remote Similarity	NPD5135	Approved
0.6602	Remote Similarity	NPD4634	Approved
0.6602	Remote Similarity	NPD5249	Phase 3
0.6566	Remote Similarity	NPD7632	Discontinued
0.6559	Remote Similarity	NPD4096	Approved
0.6548	Remote Similarity	NPD3703	Phase 2
0.6538	Remote Similarity	NPD5216	Approved
0.6538	Remote Similarity	NPD5127	Approved
0.6538	Remote Similarity	NPD5215	Approved
0.6538	Remote Similarity	NPD5217	Approved
0.6489	Remote Similarity	NPD6411	Approved
0.6484	Remote Similarity	NPD6098	Approved
0.6463	Remote Similarity	NPD4747	Approved
0.6463	Remote Similarity	NPD4244	Approved
0.6463	Remote Similarity	NPD4789	Approved
0.6463	Remote Similarity	NPD4245	Approved
0.6458	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6456	Remote Similarity	NPD3171	Clinical (unspecified phase)
0.6449	Remote Similarity	NPD6868	Approved
0.6429	Remote Similarity	NPD5696	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