NPASS Compound

Structure

NPC201359 OpenBabel07101719252D 35 39 0 0 1 0 0 0 0 0999 V2000 2.8963 -0.9898 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 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 -2.5981 -3.5000 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 -1.7321 -3.0000 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 -3.4641 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 1.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5873 -0.0388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 2 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 -3.4641 -3.0000 0.0000 C 0 0 1 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 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.6092 0.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.2079 0.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.9282 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 2 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 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.7942 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 0.7044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4612 1.7213 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9945 0.1045 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 4 27 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 6 17 2 0 0 0 0 7 20 1 0 0 0 0 8 10 1 0 0 0 0 8 18 1 0 0 0 0 9 11 1 0 0 0 0 9 19 1 0 0 0 0 10 26 1 0 0 0 0 11 27 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 21 1 0 0 0 0 13 23 1 0 0 0 0 14 22 1 0 0 0 0 14 24 1 0 0 0 0 15 21 1 0 0 0 0 15 30 2 0 0 0 0 16 2 1 1 0 0 0 16 25 1 0 0 0 0 16 34 1 0 0 0 0 17 26 1 0 0 0 0 18 35 1 6 0 0 0 19 20 1 0 0 0 0 19 26 1 6 0 0 0 20 28 1 1 0 0 0 21 27 1 6 0 0 0 22 25 1 0 0 0 0 22 33 1 6 0 0 0 23 28 1 1 0 0 0 23 31 1 0 0 0 0 24 34 1 0 0 0 0 24 35 1 1 0 0 0 25 29 1 6 0 0 0 26 3 1 6 0 0 0 27 28 1 6 0 0 0 28 32 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	491.32
Volume:	508.527
LogP:	2.574
LogD:	2.599
LogS:	-4.012
# Rotatable Bonds:	4
TPSA:	111.24
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.518
Synthetic Accessibility Score:	5.313
Fsp3:	0.893
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.772
MDCK Permeability:	2.3007216441328637e-05
Pgp-inhibitor:	0.031
Pgp-substrate:	0.979
Human Intestinal Absorption (HIA):	0.015
20% Bioavailability (F20%):	0.828
30% Bioavailability (F30%):	0.25

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.558
Plasma Protein Binding (PPB):	80.06797790527344%
Volume Distribution (VD):	1.12
Pgp-substrate:	11.353053092956543%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.191
CYP2C19-inhibitor:	0.015
CYP2C19-substrate:	0.856
CYP2C9-inhibitor:	0.032
CYP2C9-substrate:	0.023
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.562
CYP3A4-inhibitor:	0.513
CYP3A4-substrate:	0.582

ADMET: Excretion

Clearance (CL):	6.807
Half-life (T1/2):	0.528

ADMET: Toxicity

hERG Blockers:	0.398
Human Hepatotoxicity (H-HT):	0.324
Drug-inuced Liver Injury (DILI):	0.166
AMES Toxicity:	0.285
Rat Oral Acute Toxicity:	0.525
Maximum Recommended Daily Dose:	0.961
Skin Sensitization:	0.476
Carcinogencity:	0.46
Eye Corrosion:	0.005
Eye Irritation:	0.011
Respiratory Toxicity:	0.975

Download Data

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

Natural Product: NPC201359

Natural Product ID:	NPC201359
*Common Name:**	Holacurtinol
IUPAC Name:	1-[(3S,8R,9S,10R,13R,14S,15S,17S)-3-[(2R,4S,5R,6R)-5-amino-4-methoxy-6-methyloxan-2-yl]oxy-14,15-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone
Synonyms:	Holacurtinol
Standard InCHIKey:	SFUVPIJMDPWZBZ-CIOVMACQSA-N
Standard InCHI:	InChI=1S/C28H45NO6/c1-15(30)21-13-23(31)28(32)20-7-6-17-12-18(35-24-14-22(33-5)25(29)16(2)34-24)8-10-26(17,3)19(20)9-11-27(21,28)4/h6,16,18-25,31-32H,7-14,29H2,1-5H3/t16-,18+,19+,20-,21-,22+,23+,24+,25-,26+,27-,28-/m1/s1
SMILES:	CO[C@H]1C[C@H](O[C@H]2CC[C@]3(C(=CC[C@@H]4[C@@H]3CC[C@]3([C@]4(O)[C@@H](O)C[C@@H]3C(=O)C)C)C2)C)O[C@@H]([C@H]1N)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL513963
PubChem CID:	10624956
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0001013] Steroidal glycosides

*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
NPO32911	holarrhena curtisii	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[9834146]

☑ 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	5

Activity Type	# Activity
Cell Line	4
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	IC50	=	2.6	ug.mL-1	PMID[453439]
NPT168	Cell Line	P388	Mus musculus	IC50	=	16.0	ug.mL-1	PMID[453439]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.4	ug.mL-1	PMID[453439]
NPT168	Cell Line	P388	Mus musculus	IC50	=	10.0	ug.mL-1	PMID[453439]
NPT633	Organism	Leishmania donovani	Leishmania donovani	IC50	=	6.25	ug.mL-1	PMID[453439]

☑ 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 NPC201359 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	143
0.1-0.2	997
0.2-0.3	4549
0.3-0.4	14513
0.4-0.5	10768
0.5-0.6	6366
0.6-0.7	4605
0.7-0.8	749
0.8-0.85	6
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8417	Intermediate Similarity	NPC246399
0.8417	Intermediate Similarity	NPC34977
0.808	Intermediate Similarity	NPC221196
0.808	Intermediate Similarity	NPC39485
0.797	Intermediate Similarity	NPC139585
0.7907	Intermediate Similarity	NPC28532
0.7891	Intermediate Similarity	NPC471406
0.7886	Intermediate Similarity	NPC154856
0.7886	Intermediate Similarity	NPC475317
0.7886	Intermediate Similarity	NPC52241
0.7874	Intermediate Similarity	NPC475632
0.7874	Intermediate Similarity	NPC86020
0.784	Intermediate Similarity	NPC260665
0.784	Intermediate Similarity	NPC178981
0.7812	Intermediate Similarity	NPC161738
0.7786	Intermediate Similarity	NPC296686
0.7786	Intermediate Similarity	NPC803
0.7778	Intermediate Similarity	NPC477580
0.776	Intermediate Similarity	NPC474265
0.776	Intermediate Similarity	NPC210420
0.776	Intermediate Similarity	NPC130427
0.7752	Intermediate Similarity	NPC475187
0.7731	Intermediate Similarity	NPC83709
0.7727	Intermediate Similarity	NPC174367
0.7727	Intermediate Similarity	NPC47113
0.7705	Intermediate Similarity	NPC210178
0.7692	Intermediate Similarity	NPC249553
0.7692	Intermediate Similarity	NPC182900
0.7686	Intermediate Similarity	NPC98765
0.7661	Intermediate Similarity	NPC246205
0.7652	Intermediate Similarity	NPC475194
0.7638	Intermediate Similarity	NPC474557
0.7638	Intermediate Similarity	NPC473882
0.7634	Intermediate Similarity	NPC156789
0.7634	Intermediate Similarity	NPC305771
0.7634	Intermediate Similarity	NPC94072
0.7634	Intermediate Similarity	NPC15918
0.7634	Intermediate Similarity	NPC169816
0.7619	Intermediate Similarity	NPC280782
0.7612	Intermediate Similarity	NPC168899
0.7612	Intermediate Similarity	NPC311534
0.7612	Intermediate Similarity	NPC69273
0.7612	Intermediate Similarity	NPC293623
0.7606	Intermediate Similarity	NPC141669
0.76	Intermediate Similarity	NPC470065
0.7591	Intermediate Similarity	NPC477072
0.7581	Intermediate Similarity	NPC295389
0.7578	Intermediate Similarity	NPC279638
0.7576	Intermediate Similarity	NPC160084
0.7574	Intermediate Similarity	NPC473519
0.7574	Intermediate Similarity	NPC473805
0.7574	Intermediate Similarity	NPC471855
0.7571	Intermediate Similarity	NPC302276
0.7571	Intermediate Similarity	NPC180770
0.7559	Intermediate Similarity	NPC477944
0.7541	Intermediate Similarity	NPC191892
0.754	Intermediate Similarity	NPC263827
0.754	Intermediate Similarity	NPC471243
0.754	Intermediate Similarity	NPC269466
0.754	Intermediate Similarity	NPC250481
0.754	Intermediate Similarity	NPC285410
0.7537	Intermediate Similarity	NPC305496
0.752	Intermediate Similarity	NPC118225
0.7519	Intermediate Similarity	NPC473474
0.7519	Intermediate Similarity	NPC473505
0.7518	Intermediate Similarity	NPC102015
0.75	Intermediate Similarity	NPC243354
0.75	Intermediate Similarity	NPC241008
0.75	Intermediate Similarity	NPC74727
0.75	Intermediate Similarity	NPC173347
0.75	Intermediate Similarity	NPC475431
0.7481	Intermediate Similarity	NPC472257
0.748	Intermediate Similarity	NPC121566
0.748	Intermediate Similarity	NPC100955
0.748	Intermediate Similarity	NPC149124
0.748	Intermediate Similarity	NPC471244
0.748	Intermediate Similarity	NPC75531
0.748	Intermediate Similarity	NPC471245
0.7466	Intermediate Similarity	NPC298005
0.7466	Intermediate Similarity	NPC36463
0.7465	Intermediate Similarity	NPC162910
0.7462	Intermediate Similarity	NPC45475
0.746	Intermediate Similarity	NPC101450
0.746	Intermediate Similarity	NPC27551
0.746	Intermediate Similarity	NPC114961
0.746	Intermediate Similarity	NPC129340
0.7445	Intermediate Similarity	NPC475472
0.7444	Intermediate Similarity	NPC27363
0.7431	Intermediate Similarity	NPC214821
0.7431	Intermediate Similarity	NPC298067
0.7426	Intermediate Similarity	NPC471407
0.7424	Intermediate Similarity	NPC475182
0.7424	Intermediate Similarity	NPC42675
0.7424	Intermediate Similarity	NPC470921
0.7424	Intermediate Similarity	NPC202051
0.7422	Intermediate Similarity	NPC251309
0.7422	Intermediate Similarity	NPC200944
0.7422	Intermediate Similarity	NPC194100
0.7422	Intermediate Similarity	NPC62696
0.7422	Intermediate Similarity	NPC293038
0.7422	Intermediate Similarity	NPC73455
0.7419	Intermediate Similarity	NPC95243
0.7419	Intermediate Similarity	NPC12823
0.7419	Intermediate Similarity	NPC278628
0.7419	Intermediate Similarity	NPC63023
0.7419	Intermediate Similarity	NPC231530
0.7405	Intermediate Similarity	NPC319570
0.7405	Intermediate Similarity	NPC477071
0.7402	Intermediate Similarity	NPC63244
0.7402	Intermediate Similarity	NPC122339
0.7398	Intermediate Similarity	NPC475701
0.7391	Intermediate Similarity	NPC73829
0.7391	Intermediate Similarity	NPC119794
0.7388	Intermediate Similarity	NPC248202
0.7381	Intermediate Similarity	NPC477070
0.7381	Intermediate Similarity	NPC8431
0.7381	Intermediate Similarity	NPC477069
0.7381	Intermediate Similarity	NPC265655
0.7381	Intermediate Similarity	NPC469744
0.7372	Intermediate Similarity	NPC478139
0.7364	Intermediate Similarity	NPC102088
0.7364	Intermediate Similarity	NPC475633
0.7364	Intermediate Similarity	NPC472274
0.7364	Intermediate Similarity	NPC471398
0.7364	Intermediate Similarity	NPC116024
0.7361	Intermediate Similarity	NPC298469
0.736	Intermediate Similarity	NPC59530
0.736	Intermediate Similarity	NPC144459
0.736	Intermediate Similarity	NPC293512
0.736	Intermediate Similarity	NPC165873
0.7357	Intermediate Similarity	NPC145899
0.7357	Intermediate Similarity	NPC297058
0.7353	Intermediate Similarity	NPC473888
0.7348	Intermediate Similarity	NPC129393
0.7344	Intermediate Similarity	NPC37739
0.7344	Intermediate Similarity	NPC46388
0.7344	Intermediate Similarity	NPC233003
0.7344	Intermediate Similarity	NPC473303
0.7339	Intermediate Similarity	NPC474464
0.7339	Intermediate Similarity	NPC471293
0.7339	Intermediate Similarity	NPC137657
0.7338	Intermediate Similarity	NPC76999
0.7333	Intermediate Similarity	NPC93368
0.7333	Intermediate Similarity	NPC476673
0.7333	Intermediate Similarity	NPC469750
0.7333	Intermediate Similarity	NPC250556
0.7329	Intermediate Similarity	NPC61717
0.7329	Intermediate Similarity	NPC244380
0.7324	Intermediate Similarity	NPC265908
0.7323	Intermediate Similarity	NPC471476
0.7323	Intermediate Similarity	NPC163314
0.7323	Intermediate Similarity	NPC473324
0.7323	Intermediate Similarity	NPC76084
0.7319	Intermediate Similarity	NPC42670
0.7319	Intermediate Similarity	NPC19124
0.7319	Intermediate Similarity	NPC25455
0.7319	Intermediate Similarity	NPC15249
0.7317	Intermediate Similarity	NPC185530
0.7313	Intermediate Similarity	NPC238005
0.7313	Intermediate Similarity	NPC1980
0.7313	Intermediate Similarity	NPC141196
0.7313	Intermediate Similarity	NPC256983
0.7308	Intermediate Similarity	NPC88945
0.7308	Intermediate Similarity	NPC244127
0.7308	Intermediate Similarity	NPC302471
0.7302	Intermediate Similarity	NPC195708
0.7302	Intermediate Similarity	NPC272576
0.7302	Intermediate Similarity	NPC469733
0.7302	Intermediate Similarity	NPC469729
0.7302	Intermediate Similarity	NPC94529
0.7293	Intermediate Similarity	NPC476545
0.7293	Intermediate Similarity	NPC476543
0.7293	Intermediate Similarity	NPC476544
0.7287	Intermediate Similarity	NPC317210
0.7287	Intermediate Similarity	NPC47063
0.7287	Intermediate Similarity	NPC194273
0.7287	Intermediate Similarity	NPC204458
0.7287	Intermediate Similarity	NPC471173
0.7287	Intermediate Similarity	NPC269315
0.7287	Intermediate Similarity	NPC138334
0.7287	Intermediate Similarity	NPC471627
0.7287	Intermediate Similarity	NPC94141
0.7287	Intermediate Similarity	NPC255017
0.7287	Intermediate Similarity	NPC189884
0.7287	Intermediate Similarity	NPC962
0.7287	Intermediate Similarity	NPC271138
0.7286	Intermediate Similarity	NPC235772
0.7286	Intermediate Similarity	NPC75318
0.7286	Intermediate Similarity	NPC280941
0.728	Intermediate Similarity	NPC162033
0.728	Intermediate Similarity	NPC474015
0.728	Intermediate Similarity	NPC242748
0.728	Intermediate Similarity	NPC26798
0.728	Intermediate Similarity	NPC474569
0.728	Intermediate Similarity	NPC149047
0.728	Intermediate Similarity	NPC4115
0.728	Intermediate Similarity	NPC196528
0.7279	Intermediate Similarity	NPC240070
0.7279	Intermediate Similarity	NPC471356
0.7279	Intermediate Similarity	NPC329784

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 NPC201359 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	109
0.1-0.2	886
0.2-0.3	3702
0.3-0.4	3075
0.4-0.5	846
0.5-0.6	313
0.6-0.7	200
0.7-0.8	19
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7642	Intermediate Similarity	NPD6412	Phase 2
0.75	Intermediate Similarity	NPD6370	Approved
0.7372	Intermediate Similarity	NPD6914	Discontinued
0.7353	Intermediate Similarity	NPD7736	Approved
0.7348	Intermediate Similarity	NPD6054	Approved
0.7348	Intermediate Similarity	NPD6059	Approved
0.7333	Intermediate Similarity	NPD7507	Approved
0.7279	Intermediate Similarity	NPD8293	Discontinued
0.7266	Intermediate Similarity	NPD8449	Approved
0.7214	Intermediate Similarity	NPD8450	Suspended
0.7174	Intermediate Similarity	NPD7319	Approved
0.7164	Intermediate Similarity	NPD6908	Approved
0.7164	Intermediate Similarity	NPD6016	Approved
0.7164	Intermediate Similarity	NPD6015	Approved
0.7164	Intermediate Similarity	NPD6909	Approved
0.7132	Intermediate Similarity	NPD7492	Approved
0.7111	Intermediate Similarity	NPD5988	Approved
0.708	Intermediate Similarity	NPD6616	Approved
0.7077	Intermediate Similarity	NPD6882	Approved
0.7029	Intermediate Similarity	NPD7078	Approved
0.7008	Intermediate Similarity	NPD5739	Approved
0.7008	Intermediate Similarity	NPD6402	Approved
0.7008	Intermediate Similarity	NPD6675	Approved
0.7008	Intermediate Similarity	NPD7128	Approved
0.6992	Remote Similarity	NPD6009	Approved
0.6977	Remote Similarity	NPD6373	Approved
0.6977	Remote Similarity	NPD6372	Approved
0.6977	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6963	Remote Similarity	NPD6319	Approved
0.6934	Remote Similarity	NPD8328	Phase 3
0.6934	Remote Similarity	NPD7604	Phase 2
0.6923	Remote Similarity	NPD4634	Approved
0.6899	Remote Similarity	NPD6899	Approved
0.6899	Remote Similarity	NPD6881	Approved
0.6899	Remote Similarity	NPD7320	Approved
0.6894	Remote Similarity	NPD4632	Approved
0.6875	Remote Similarity	NPD6008	Approved
0.687	Remote Similarity	NPD6650	Approved
0.687	Remote Similarity	NPD6649	Approved
0.6866	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD8337	Approved
0.6857	Remote Similarity	NPD6033	Approved
0.6857	Remote Similarity	NPD8336	Approved
0.6855	Remote Similarity	NPD4755	Approved
0.6822	Remote Similarity	NPD5697	Approved
0.6822	Remote Similarity	NPD5701	Approved
0.6818	Remote Similarity	NPD8297	Approved
0.6815	Remote Similarity	NPD7328	Approved
0.6815	Remote Similarity	NPD7327	Approved
0.6812	Remote Similarity	NPD6067	Discontinued
0.6794	Remote Similarity	NPD6883	Approved
0.6794	Remote Similarity	NPD7102	Approved
0.6794	Remote Similarity	NPD7290	Approved
0.6788	Remote Similarity	NPD8033	Approved
0.6783	Remote Similarity	NPD8338	Approved
0.6767	Remote Similarity	NPD8133	Approved
0.6765	Remote Similarity	NPD7516	Approved
0.6746	Remote Similarity	NPD5285	Approved
0.6746	Remote Similarity	NPD4700	Approved
0.6746	Remote Similarity	NPD5286	Approved
0.6746	Remote Similarity	NPD4696	Approved
0.6742	Remote Similarity	NPD6847	Approved
0.6742	Remote Similarity	NPD6617	Approved
0.6742	Remote Similarity	NPD8130	Phase 1
0.6742	Remote Similarity	NPD6869	Approved
0.6718	Remote Similarity	NPD6012	Approved
0.6718	Remote Similarity	NPD6013	Approved
0.6718	Remote Similarity	NPD6014	Approved
0.6715	Remote Similarity	NPD8294	Approved
0.6715	Remote Similarity	NPD8377	Approved
0.6694	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD8296	Approved
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD8380	Approved
0.6667	Remote Similarity	NPD8335	Approved
0.6667	Remote Similarity	NPD8379	Approved
0.6667	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6940	Discontinued
0.6667	Remote Similarity	NPD7503	Approved
0.6667	Remote Similarity	NPD8378	Approved
0.6641	Remote Similarity	NPD5211	Phase 2
0.6641	Remote Similarity	NPD5225	Approved
0.6641	Remote Similarity	NPD5224	Approved
0.6641	Remote Similarity	NPD4633	Approved
0.6641	Remote Similarity	NPD6011	Approved
0.6641	Remote Similarity	NPD5226	Approved
0.6618	Remote Similarity	NPD7115	Discovery
0.6617	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6589	Remote Similarity	NPD5174	Approved
0.6589	Remote Similarity	NPD5175	Approved
0.6587	Remote Similarity	NPD6083	Phase 2
0.6587	Remote Similarity	NPD6084	Phase 2
0.6585	Remote Similarity	NPD6079	Approved
0.6562	Remote Similarity	NPD5223	Approved
0.6555	Remote Similarity	NPD4786	Approved
0.6554	Remote Similarity	NPD6333	Approved
0.6554	Remote Similarity	NPD6334	Approved
0.6547	Remote Similarity	NPD5983	Phase 2
0.6547	Remote Similarity	NPD8444	Approved
0.6538	Remote Similarity	NPD5141	Approved
0.6532	Remote Similarity	NPD4202	Approved
0.6515	Remote Similarity	NPD6686	Approved
0.6508	Remote Similarity	NPD4697	Phase 3
0.6489	Remote Similarity	NPD4767	Approved
0.6489	Remote Similarity	NPD4768	Approved
0.6479	Remote Similarity	NPD6336	Discontinued
0.6462	Remote Similarity	NPD4754	Approved
0.6454	Remote Similarity	NPD7122	Discontinued
0.6454	Remote Similarity	NPD7829	Approved
0.6454	Remote Similarity	NPD7830	Approved
0.6449	Remote Similarity	NPD7641	Discontinued
0.6446	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD8516	Approved
0.6429	Remote Similarity	NPD8517	Approved
0.6429	Remote Similarity	NPD8515	Approved
0.6429	Remote Similarity	NPD8513	Phase 3
0.6423	Remote Similarity	NPD6274	Approved
0.6423	Remote Similarity	NPD4753	Phase 2
0.6414	Remote Similarity	NPD8391	Approved
0.6414	Remote Similarity	NPD8390	Approved
0.6414	Remote Similarity	NPD8392	Approved
0.6408	Remote Similarity	NPD8340	Approved
0.6408	Remote Similarity	NPD8342	Approved
0.6408	Remote Similarity	NPD8341	Approved
0.6408	Remote Similarity	NPD8299	Approved
0.6406	Remote Similarity	NPD7638	Approved
0.6406	Remote Similarity	NPD5696	Approved
0.6403	Remote Similarity	NPD7101	Approved
0.6403	Remote Similarity	NPD7100	Approved
0.6391	Remote Similarity	NPD4730	Approved
0.6391	Remote Similarity	NPD4729	Approved
0.6391	Remote Similarity	NPD5128	Approved
0.6387	Remote Similarity	NPD3667	Approved
0.6378	Remote Similarity	NPD5222	Approved
0.6378	Remote Similarity	NPD5221	Approved
0.6378	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6377	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD8451	Approved
0.6357	Remote Similarity	NPD7639	Approved
0.6357	Remote Similarity	NPD7640	Approved
0.6331	Remote Similarity	NPD6335	Approved
0.6328	Remote Similarity	NPD5173	Approved
0.6323	Remote Similarity	NPD7625	Phase 1
0.6319	Remote Similarity	NPD8448	Approved
0.6319	Remote Similarity	NPD8074	Phase 3
0.6312	Remote Similarity	NPD8267	Approved
0.6312	Remote Similarity	NPD8268	Approved
0.6312	Remote Similarity	NPD8266	Approved
0.6312	Remote Similarity	NPD6921	Approved
0.6312	Remote Similarity	NPD8274	Clinical (unspecified phase)
0.6312	Remote Similarity	NPD8269	Approved
0.6299	Remote Similarity	NPD5210	Approved
0.6299	Remote Similarity	NPD5695	Phase 3
0.6299	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6299	Remote Similarity	NPD4629	Approved
0.6296	Remote Similarity	NPD5248	Approved
0.6296	Remote Similarity	NPD5247	Approved
0.6296	Remote Similarity	NPD5249	Phase 3
0.6296	Remote Similarity	NPD5251	Approved
0.6296	Remote Similarity	NPD5250	Approved
0.6281	Remote Similarity	NPD3133	Approved
0.6281	Remote Similarity	NPD3665	Phase 1
0.6281	Remote Similarity	NPD3666	Approved
0.6269	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6268	Remote Similarity	NPD8080	Discontinued
0.6259	Remote Similarity	NPD6317	Approved
0.625	Remote Similarity	NPD5215	Approved
0.625	Remote Similarity	NPD5217	Approved
0.625	Remote Similarity	NPD5216	Approved
0.6241	Remote Similarity	NPD7147	Phase 3
0.6241	Remote Similarity	NPD7148	Clinical (unspecified phase)
0.622	Remote Similarity	NPD7748	Approved
0.6214	Remote Similarity	NPD6314	Approved
0.6214	Remote Similarity	NPD6313	Approved
0.621	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6429	Approved
0.6204	Remote Similarity	NPD6053	Discontinued
0.6204	Remote Similarity	NPD6430	Approved
0.6202	Remote Similarity	NPD7902	Approved
0.6197	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.619	Remote Similarity	NPD8034	Phase 2
0.619	Remote Similarity	NPD5956	Approved
0.619	Remote Similarity	NPD7515	Phase 2
0.619	Remote Similarity	NPD8035	Phase 2
0.6179	Remote Similarity	NPD7146	Approved
0.6179	Remote Similarity	NPD5330	Approved
0.6179	Remote Similarity	NPD6684	Approved
0.6179	Remote Similarity	NPD6409	Approved
0.6179	Remote Similarity	NPD7334	Approved
0.6179	Remote Similarity	NPD7521	Approved
0.6176	Remote Similarity	NPD5169	Approved
0.6176	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5135	Approved
0.6149	Remote Similarity	NPD7260	Phase 2
0.6131	Remote Similarity	NPD5127	Approved
0.6116	Remote Similarity	NPD4223	Phase 3
0.6116	Remote Similarity	NPD4221	Approved
0.6111	Remote Similarity	NPD7642	Approved
0.6098	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD5329	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