NPASS Compound

Structure

NPC470065 OpenBabel07101719132D 37 41 0 0 1 0 0 0 0 0999 V2000 7.7115 -0.1863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2460 -1.7610 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8138 3.1884 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2205 2.2749 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5348 -0.4612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -1.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 1.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 -1.8366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7861 1.9305 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7807 1.8259 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9886 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 -2.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 -0.6522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6581 1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5867 0.3478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4013 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.3794 1.0169 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.2079 0.9781 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.9886 0.8478 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8546 -0.6522 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.5867 -0.6522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.4527 -2.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 0.8478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.1215 1.3849 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9945 -0.1045 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 7.4527 -1.1522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2260 2.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1226 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7206 -1.1522 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8546 0.3478 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 8.3187 -2.6522 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7206 1.8478 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9305 0.7971 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4170 2.9672 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4945 -0.9706 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 27 1 0 0 0 0 2 27 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 8 36 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 2 0 0 0 0 11 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 23 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 16 24 1 0 0 0 0 17 15 1 1 0 0 0 17 18 1 0 0 0 0 17 26 1 0 0 0 0 18 29 1 1 0 0 0 19 25 1 1 0 0 0 19 37 1 0 0 0 0 20 29 1 0 0 0 0 20 31 1 0 0 0 0 21 30 1 1 0 0 0 21 31 1 0 0 0 0 22 27 1 0 0 0 0 22 30 1 1 0 0 0 23 27 1 0 0 0 0 23 32 2 0 0 0 0 24 31 1 6 0 0 0 24 33 1 0 0 0 0 25 28 1 0 0 0 0 25 34 1 6 0 0 0 26 36 1 6 0 0 0 26 37 1 0 0 0 0 28 35 1 0 0 0 0 29 5 1 6 0 0 0 30 6 1 1 0 0 0 31 7 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	518.36
Volume:	549.418
LogP:	3.214
LogD:	3.25
LogS:	-4.209
# Rotatable Bonds:	4
TPSA:	96.22
# H-Bond Aceptor:	6
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.469
Synthetic Accessibility Score:	5.346
Fsp3:	0.903
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.879
MDCK Permeability:	1.0450610716361552e-05
Pgp-inhibitor:	0.979
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.294
30% Bioavailability (F30%):	0.942

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.106
Plasma Protein Binding (PPB):	84.2606430053711%
Volume Distribution (VD):	1.53
Pgp-substrate:	8.716252326965332%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.32
CYP2C19-inhibitor:	0.01
CYP2C19-substrate:	0.842
CYP2C9-inhibitor:	0.053
CYP2C9-substrate:	0.125
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.096
CYP3A4-inhibitor:	0.322
CYP3A4-substrate:	0.326

ADMET: Excretion

Clearance (CL):	4.101
Half-life (T1/2):	0.75

ADMET: Toxicity

hERG Blockers:	0.016
Human Hepatotoxicity (H-HT):	0.299
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.029
Rat Oral Acute Toxicity:	0.868
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.229
Carcinogencity:	0.017
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC470065

Natural Product ID:	NPC470065
*Common Name:**	3-O-Acetyl-21-O-Methyltoosendanpentol
IUPAC Name:	(5R,7R,8R,9R,10R,13S,17R)-17-[(2R,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-7-hydroxy-4,4,8,10,13-pentamethyl-1,2,5,6,7,9,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-one
Synonyms:
Standard InCHIKey:	UTGJQBYMUPRIKQ-VMPVCBGCSA-N
Standard InCHI:	InChI=1S/C31H50O6/c1-27(2)22-16-24(33)31(7)20-10-9-18(17-15-19(37-26(17)36-8)25(34)28(3,4)35)29(20,5)13-11-21(31)30(22,6)14-12-23(27)32/h10,17-19,21-22,24-26,33-35H,9,11-16H2,1-8H3/t17-,18+,19+,21+,22-,24+,25-,26+,29-,30+,31-/m0/s1
SMILES:	CC1(C2CC(C3(C(C2(CCC1=O)C)CCC4(C3=CCC4C5CC(OC5OC)C(C(C)(C)O)O)C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1668618
PubChem CID:	53319631
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids [CHEMONTID:0002380] Limonoids

*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
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19943621]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	twigs	Xishuangbanna, Yunnan, China	2007-May	PMID[21288727]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32208696]
NPO19151	Chisocheton paniculatus	Species	Meliaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	18200.0	nM	PMID[484958]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	57500.0	nM	PMID[484958]

☑ 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 NPC470065 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	224
0.1-0.2	1447
0.2-0.3	4843
0.3-0.4	9270
0.4-0.5	11716
0.5-0.6	6230
0.6-0.7	5215
0.7-0.8	3401
0.8-0.85	300
0.85-0.9	49
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9167	High Similarity	NPC302471
0.9048	High Similarity	NPC469845
0.8942	High Similarity	NPC470057
0.8942	High Similarity	NPC470061
0.8942	High Similarity	NPC470043
0.8942	High Similarity	NPC470058
0.8942	High Similarity	NPC470059
0.8942	High Similarity	NPC470060
0.8942	High Similarity	NPC470062
0.8942	High Similarity	NPC470064
0.8942	High Similarity	NPC100955
0.8942	High Similarity	NPC121566
0.8919	High Similarity	NPC161065
0.8899	High Similarity	NPC477580
0.8879	High Similarity	NPC101450
0.8857	High Similarity	NPC95243
0.8857	High Similarity	NPC63023
0.8839	High Similarity	NPC241192
0.8807	High Similarity	NPC471173
0.8807	High Similarity	NPC471627
0.8727	High Similarity	NPC472274
0.8704	High Similarity	NPC52241
0.8704	High Similarity	NPC475317
0.8704	High Similarity	NPC154856
0.8679	High Similarity	NPC210178
0.8679	High Similarity	NPC472655
0.8667	High Similarity	NPC471005
0.8547	High Similarity	NPC298841
0.8545	High Similarity	NPC210420
0.8545	High Similarity	NPC474265
0.8545	High Similarity	NPC130427
0.8532	High Similarity	NPC5284
0.8519	High Similarity	NPC258323
0.8505	High Similarity	NPC470055
0.8505	High Similarity	NPC470056
0.8482	Intermediate Similarity	NPC243981
0.8468	Intermediate Similarity	NPC293038
0.8468	Intermediate Similarity	NPC178981
0.8468	Intermediate Similarity	NPC255017
0.8468	Intermediate Similarity	NPC62696
0.8462	Intermediate Similarity	NPC5358
0.8462	Intermediate Similarity	NPC216260
0.844	Intermediate Similarity	NPC246205
0.844	Intermediate Similarity	NPC118225
0.844	Intermediate Similarity	NPC218853
0.8426	Intermediate Similarity	NPC293512
0.8426	Intermediate Similarity	NPC59530
0.8421	Intermediate Similarity	NPC161738
0.8421	Intermediate Similarity	NPC477071
0.8411	Intermediate Similarity	NPC31430
0.8411	Intermediate Similarity	NPC471293
0.8411	Intermediate Similarity	NPC85593
0.8393	Intermediate Similarity	NPC102088
0.8393	Intermediate Similarity	NPC474557
0.8393	Intermediate Similarity	NPC473882
0.8378	Intermediate Similarity	NPC234042
0.8378	Intermediate Similarity	NPC152117
0.8364	Intermediate Similarity	NPC250956
0.8349	Intermediate Similarity	NPC272576
0.8349	Intermediate Similarity	NPC473288
0.8349	Intermediate Similarity	NPC295389
0.8349	Intermediate Similarity	NPC469844
0.8333	Intermediate Similarity	NPC470587
0.8319	Intermediate Similarity	NPC279638
0.8318	Intermediate Similarity	NPC213190
0.8305	Intermediate Similarity	NPC47113
0.8305	Intermediate Similarity	NPC174367
0.8304	Intermediate Similarity	NPC260665
0.8302	Intermediate Similarity	NPC470054
0.8291	Intermediate Similarity	NPC27363
0.8288	Intermediate Similarity	NPC263827
0.8288	Intermediate Similarity	NPC285410
0.8288	Intermediate Similarity	NPC272242
0.8288	Intermediate Similarity	NPC250481
0.8288	Intermediate Similarity	NPC269466
0.8276	Intermediate Similarity	NPC182900
0.8276	Intermediate Similarity	NPC249553
0.8273	Intermediate Similarity	NPC477070
0.8273	Intermediate Similarity	NPC477069
0.8273	Intermediate Similarity	NPC8431
0.8241	Intermediate Similarity	NPC222161
0.8235	Intermediate Similarity	NPC42399
0.8235	Intermediate Similarity	NPC473166
0.823	Intermediate Similarity	NPC165439
0.823	Intermediate Similarity	NPC475633
0.823	Intermediate Similarity	NPC74727
0.8224	Intermediate Similarity	NPC470053
0.8224	Intermediate Similarity	NPC136816
0.8214	Intermediate Similarity	NPC46388
0.8214	Intermediate Similarity	NPC471245
0.8214	Intermediate Similarity	NPC37739
0.8214	Intermediate Similarity	NPC174836
0.8208	Intermediate Similarity	NPC324598
0.8205	Intermediate Similarity	NPC28532
0.8205	Intermediate Similarity	NPC169816
0.8205	Intermediate Similarity	NPC15918
0.8205	Intermediate Similarity	NPC305771
0.8205	Intermediate Similarity	NPC94072
0.8198	Intermediate Similarity	NPC274507
0.8198	Intermediate Similarity	NPC129340
0.819	Intermediate Similarity	NPC472257
0.819	Intermediate Similarity	NPC471406
0.8182	Intermediate Similarity	NPC94942
0.8182	Intermediate Similarity	NPC230888
0.8174	Intermediate Similarity	NPC239293
0.8173	Intermediate Similarity	NPC180557
0.8173	Intermediate Similarity	NPC37787
0.8173	Intermediate Similarity	NPC473415
0.8173	Intermediate Similarity	NPC30677
0.8173	Intermediate Similarity	NPC469329
0.8167	Intermediate Similarity	NPC311534
0.8165	Intermediate Similarity	NPC473199
0.8158	Intermediate Similarity	NPC134869
0.8158	Intermediate Similarity	NPC152199
0.8158	Intermediate Similarity	NPC235539
0.8155	Intermediate Similarity	NPC198074
0.8155	Intermediate Similarity	NPC274046
0.8151	Intermediate Similarity	NPC469750
0.8151	Intermediate Similarity	NPC250556
0.8142	Intermediate Similarity	NPC269315
0.8142	Intermediate Similarity	NPC189884
0.8142	Intermediate Similarity	NPC204458
0.8142	Intermediate Similarity	NPC251309
0.8142	Intermediate Similarity	NPC47063
0.8142	Intermediate Similarity	NPC271138
0.8142	Intermediate Similarity	NPC102619
0.8142	Intermediate Similarity	NPC477944
0.8142	Intermediate Similarity	NPC311592
0.8142	Intermediate Similarity	NPC75167
0.8142	Intermediate Similarity	NPC138334
0.8131	Intermediate Similarity	NPC309425
0.8131	Intermediate Similarity	NPC47566
0.8131	Intermediate Similarity	NPC129372
0.8131	Intermediate Similarity	NPC88000
0.8131	Intermediate Similarity	NPC4831
0.8131	Intermediate Similarity	NPC472023
0.8131	Intermediate Similarity	NPC160734
0.8125	Intermediate Similarity	NPC477073
0.8125	Intermediate Similarity	NPC471243
0.8125	Intermediate Similarity	NPC108748
0.8125	Intermediate Similarity	NPC190837
0.8125	Intermediate Similarity	NPC297208
0.8125	Intermediate Similarity	NPC122339
0.8125	Intermediate Similarity	NPC201992
0.8125	Intermediate Similarity	NPC30397
0.8125	Intermediate Similarity	NPC235841
0.8125	Intermediate Similarity	NPC274833
0.8125	Intermediate Similarity	NPC211798
0.8125	Intermediate Similarity	NPC191763
0.8125	Intermediate Similarity	NPC473481
0.812	Intermediate Similarity	NPC476672
0.812	Intermediate Similarity	NPC202051
0.812	Intermediate Similarity	NPC204731
0.8113	Intermediate Similarity	NPC470068
0.8113	Intermediate Similarity	NPC470066
0.8113	Intermediate Similarity	NPC470067
0.8113	Intermediate Similarity	NPC234287
0.8113	Intermediate Similarity	NPC280825
0.8108	Intermediate Similarity	NPC41405
0.8108	Intermediate Similarity	NPC204407
0.8108	Intermediate Similarity	NPC265655
0.8108	Intermediate Similarity	NPC57362
0.8108	Intermediate Similarity	NPC143706
0.8108	Intermediate Similarity	NPC167383
0.8108	Intermediate Similarity	NPC306746
0.8108	Intermediate Similarity	NPC237503
0.8108	Intermediate Similarity	NPC137917
0.8108	Intermediate Similarity	NPC472534
0.8103	Intermediate Similarity	NPC122971
0.8103	Intermediate Similarity	NPC178548
0.8103	Intermediate Similarity	NPC258592
0.8091	Intermediate Similarity	NPC283849
0.8091	Intermediate Similarity	NPC473165
0.8087	Intermediate Similarity	NPC13713
0.8087	Intermediate Similarity	NPC477252
0.8087	Intermediate Similarity	NPC309433
0.8083	Intermediate Similarity	NPC305496
0.8083	Intermediate Similarity	NPC471357
0.8083	Intermediate Similarity	NPC117702
0.8083	Intermediate Similarity	NPC329784
0.8083	Intermediate Similarity	NPC240070
0.8083	Intermediate Similarity	NPC179412
0.8083	Intermediate Similarity	NPC146456
0.8083	Intermediate Similarity	NPC469757
0.8083	Intermediate Similarity	NPC471356
0.8077	Intermediate Similarity	NPC240617
0.807	Intermediate Similarity	NPC475163
0.807	Intermediate Similarity	NPC116024
0.807	Intermediate Similarity	NPC181145
0.807	Intermediate Similarity	NPC474906
0.807	Intermediate Similarity	NPC326542
0.807	Intermediate Similarity	NPC18547
0.8067	Intermediate Similarity	NPC473505
0.8067	Intermediate Similarity	NPC475194
0.8067	Intermediate Similarity	NPC476674
0.8053	Intermediate Similarity	NPC161434
0.8053	Intermediate Similarity	NPC473303
0.8053	Intermediate Similarity	NPC212968
0.8053	Intermediate Similarity	NPC64106
0.8053	Intermediate Similarity	NPC195132

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 NPC470065 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	194
0.1-0.2	1766
0.2-0.3	3989
0.3-0.4	2072
0.4-0.5	609
0.5-0.6	243
0.6-0.7	186
0.7-0.8	89
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8362	Intermediate Similarity	NPD6370	Approved
0.819	Intermediate Similarity	NPD6059	Approved
0.819	Intermediate Similarity	NPD6054	Approved
0.8167	Intermediate Similarity	NPD7736	Approved
0.8151	Intermediate Similarity	NPD7507	Approved
0.8091	Intermediate Similarity	NPD6412	Phase 2
0.8083	Intermediate Similarity	NPD8293	Discontinued
0.7966	Intermediate Similarity	NPD6016	Approved
0.7966	Intermediate Similarity	NPD6015	Approved
0.7951	Intermediate Similarity	NPD7319	Approved
0.7917	Intermediate Similarity	NPD7492	Approved
0.7899	Intermediate Similarity	NPD5988	Approved
0.7851	Intermediate Similarity	NPD6616	Approved
0.7788	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7787	Intermediate Similarity	NPD7078	Approved
0.7778	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7748	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7686	Intermediate Similarity	NPD8328	Phase 3
0.7627	Intermediate Similarity	NPD6009	Approved
0.7586	Intermediate Similarity	NPD6882	Approved
0.7581	Intermediate Similarity	NPD6033	Approved
0.7563	Intermediate Similarity	NPD7328	Approved
0.7563	Intermediate Similarity	NPD7327	Approved
0.7544	Intermediate Similarity	NPD6686	Approved
0.7544	Intermediate Similarity	NPD7320	Approved
0.7541	Intermediate Similarity	NPD6067	Discontinued
0.7522	Intermediate Similarity	NPD7128	Approved
0.7522	Intermediate Similarity	NPD6402	Approved
0.7522	Intermediate Similarity	NPD5739	Approved
0.7522	Intermediate Similarity	NPD6008	Approved
0.7522	Intermediate Similarity	NPD6675	Approved
0.7521	Intermediate Similarity	NPD4632	Approved
0.7521	Intermediate Similarity	NPD8033	Approved
0.7521	Intermediate Similarity	NPD8133	Approved
0.75	Intermediate Similarity	NPD7516	Approved
0.7438	Intermediate Similarity	NPD6319	Approved
0.7438	Intermediate Similarity	NPD8377	Approved
0.7438	Intermediate Similarity	NPD8294	Approved
0.7436	Intermediate Similarity	NPD8297	Approved
0.7391	Intermediate Similarity	NPD6899	Approved
0.7391	Intermediate Similarity	NPD6881	Approved
0.7377	Intermediate Similarity	NPD8378	Approved
0.7377	Intermediate Similarity	NPD8380	Approved
0.7377	Intermediate Similarity	NPD8335	Approved
0.7377	Intermediate Similarity	NPD8379	Approved
0.7377	Intermediate Similarity	NPD8296	Approved
0.7364	Intermediate Similarity	NPD4755	Approved
0.7358	Intermediate Similarity	NPD5328	Approved
0.7328	Intermediate Similarity	NPD6372	Approved
0.7328	Intermediate Similarity	NPD6373	Approved
0.7315	Intermediate Similarity	NPD6399	Phase 3
0.7304	Intermediate Similarity	NPD5701	Approved
0.7304	Intermediate Similarity	NPD5697	Approved
0.7265	Intermediate Similarity	NPD6883	Approved
0.7265	Intermediate Similarity	NPD7290	Approved
0.7265	Intermediate Similarity	NPD7102	Approved
0.7265	Intermediate Similarity	NPD4634	Approved
0.7241	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD4696	Approved
0.7232	Intermediate Similarity	NPD5285	Approved
0.7232	Intermediate Similarity	NPD5286	Approved
0.7232	Intermediate Similarity	NPD4700	Approved
0.7222	Intermediate Similarity	NPD6079	Approved
0.7212	Intermediate Similarity	NPD4786	Approved
0.7203	Intermediate Similarity	NPD8130	Phase 1
0.7203	Intermediate Similarity	NPD6649	Approved
0.7203	Intermediate Similarity	NPD6847	Approved
0.7203	Intermediate Similarity	NPD6617	Approved
0.7203	Intermediate Similarity	NPD6869	Approved
0.7203	Intermediate Similarity	NPD6650	Approved
0.7179	Intermediate Similarity	NPD6014	Approved
0.7179	Intermediate Similarity	NPD6012	Approved
0.7179	Intermediate Similarity	NPD6013	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.712	Intermediate Similarity	NPD7604	Phase 2
0.7105	Intermediate Similarity	NPD5224	Approved
0.7105	Intermediate Similarity	NPD5211	Phase 2
0.7105	Intermediate Similarity	NPD5225	Approved
0.7105	Intermediate Similarity	NPD5226	Approved
0.7105	Intermediate Similarity	NPD4633	Approved
0.7097	Intermediate Similarity	NPD8515	Approved
0.7097	Intermediate Similarity	NPD8513	Phase 3
0.7097	Intermediate Similarity	NPD8516	Approved
0.7097	Intermediate Similarity	NPD5983	Phase 2
0.7097	Intermediate Similarity	NPD8517	Approved
0.7094	Intermediate Similarity	NPD6011	Approved
0.708	Intermediate Similarity	NPD7639	Approved
0.708	Intermediate Similarity	NPD7640	Approved
0.7059	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7115	Discovery
0.7043	Intermediate Similarity	NPD5175	Approved
0.7043	Intermediate Similarity	NPD5174	Approved
0.7034	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7019	Intermediate Similarity	NPD3667	Approved
0.7018	Intermediate Similarity	NPD5223	Approved
0.7008	Intermediate Similarity	NPD6336	Discontinued
0.7	Intermediate Similarity	NPD4202	Approved
0.699	Remote Similarity	NPD7525	Registered
0.6983	Remote Similarity	NPD5141	Approved
0.6964	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5221	Approved
0.6964	Remote Similarity	NPD4697	Phase 3
0.6964	Remote Similarity	NPD5222	Approved
0.696	Remote Similarity	NPD7503	Approved
0.6937	Remote Similarity	NPD7748	Approved
0.6923	Remote Similarity	NPD4768	Approved
0.6923	Remote Similarity	NPD4767	Approved
0.6916	Remote Similarity	NPD3618	Phase 1
0.6909	Remote Similarity	NPD7515	Phase 2
0.6909	Remote Similarity	NPD8035	Phase 2
0.6909	Remote Similarity	NPD8034	Phase 2
0.6903	Remote Similarity	NPD7902	Approved
0.6903	Remote Similarity	NPD5173	Approved
0.6903	Remote Similarity	NPD6083	Phase 2
0.6903	Remote Similarity	NPD6084	Phase 2
0.6897	Remote Similarity	NPD4754	Approved
0.6847	Remote Similarity	NPD8171	Discontinued
0.6829	Remote Similarity	NPD6274	Approved
0.6822	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD4729	Approved
0.6807	Remote Similarity	NPD4730	Approved
0.6807	Remote Similarity	NPD5128	Approved
0.68	Remote Similarity	NPD7101	Approved
0.68	Remote Similarity	NPD7100	Approved
0.6794	Remote Similarity	NPD5956	Approved
0.6727	Remote Similarity	NPD4753	Phase 2
0.6726	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6721	Remote Similarity	NPD6053	Discontinued
0.672	Remote Similarity	NPD6335	Approved
0.6697	Remote Similarity	NPD7524	Approved
0.6696	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD5251	Approved
0.6694	Remote Similarity	NPD5248	Approved
0.6694	Remote Similarity	NPD5249	Phase 3
0.6694	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6694	Remote Similarity	NPD5247	Approved
0.6694	Remote Similarity	NPD5250	Approved
0.6693	Remote Similarity	NPD6909	Approved
0.6693	Remote Similarity	NPD6908	Approved
0.6693	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD3703	Phase 2
0.664	Remote Similarity	NPD6317	Approved
0.6639	Remote Similarity	NPD5216	Approved
0.6639	Remote Similarity	NPD5217	Approved
0.6639	Remote Similarity	NPD5215	Approved
0.6637	Remote Similarity	NPD7900	Approved
0.6637	Remote Similarity	NPD5282	Discontinued
0.6637	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6114	Approved
0.6635	Remote Similarity	NPD6115	Approved
0.6635	Remote Similarity	NPD6697	Approved
0.6635	Remote Similarity	NPD6118	Approved
0.6607	Remote Similarity	NPD6411	Approved
0.6587	Remote Similarity	NPD6314	Approved
0.6587	Remote Similarity	NPD6313	Approved
0.6579	Remote Similarity	NPD5695	Phase 3
0.6574	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD3666	Approved
0.6574	Remote Similarity	NPD3133	Approved
0.6574	Remote Similarity	NPD3668	Phase 3
0.6574	Remote Similarity	NPD3665	Phase 1
0.6565	Remote Similarity	NPD8074	Phase 3
0.6562	Remote Similarity	NPD6921	Approved
0.656	Remote Similarity	NPD6868	Approved
0.6557	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6557	Remote Similarity	NPD5135	Approved
0.6557	Remote Similarity	NPD5169	Approved
0.6552	Remote Similarity	NPD5696	Approved
0.6538	Remote Similarity	NPD6116	Phase 1
0.6509	Remote Similarity	NPD6928	Phase 2
0.6504	Remote Similarity	NPD5127	Approved
0.6504	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD6672	Approved
0.6486	Remote Similarity	NPD6903	Approved
0.6486	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6486	Remote Similarity	NPD5737	Approved
0.6481	Remote Similarity	NPD4788	Approved
0.6481	Remote Similarity	NPD6695	Phase 3
0.6455	Remote Similarity	NPD6684	Approved
0.6455	Remote Similarity	NPD7521	Approved
0.6455	Remote Similarity	NPD5330	Approved
0.6455	Remote Similarity	NPD7146	Approved
0.6455	Remote Similarity	NPD7334	Approved
0.6455	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6409	Approved
0.6446	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6117	Approved
0.6435	Remote Similarity	NPD5210	Approved
0.6435	Remote Similarity	NPD4629	Approved
0.6429	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD6101	Approved
0.6429	Remote Similarity	NPD6940	Discontinued
0.6423	Remote Similarity	NPD6371	Approved
0.6415	Remote Similarity	NPD7645	Phase 2
0.6404	Remote Similarity	NPD5778	Approved
0.6404	Remote Similarity	NPD5779	Approved
0.6396	Remote Similarity	NPD3573	Approved
0.6393	Remote Similarity	NPD5168	Approved
0.6389	Remote Similarity	NPD4221	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