NPASS Compound

Structure

NPC472257 OpenBabel07101719142D 44 49 0 0 1 0 0 0 0 0999 V2000 4.4826 3.8986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1299 4.4338 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7624 0.5102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0981 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1285 1.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3198 0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1225 2.2044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0739 2.4781 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 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4607 3.6907 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4533 1.4612 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1006 1.9965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0685 2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 1 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 2.4752 1.6691 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.7698 2.7396 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 1 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 5.4096 1.0454 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5685 3.4487 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.7479 2.5317 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 2 0 0 0 0 2 17 1 0 0 0 0 4 31 1 0 0 0 0 5 31 1 0 0 0 0 6 32 1 0 0 0 0 8 9 1 0 0 0 0 8 22 1 0 0 0 0 9 23 2 0 0 0 0 10 11 1 0 0 0 0 10 25 1 0 0 0 0 11 34 1 0 0 0 0 12 18 1 0 0 0 0 12 19 1 0 0 0 0 13 20 1 0 0 0 0 13 32 1 0 0 0 0 14 24 1 0 0 0 0 14 33 1 0 0 0 0 15 21 1 0 0 0 0 15 43 1 0 0 0 0 16 34 1 0 0 0 0 17 27 1 0 0 0 0 18 3 1 1 0 0 0 18 26 1 0 0 0 0 19 27 1 0 0 0 0 19 36 2 0 0 0 0 20 26 1 0 0 0 0 20 37 2 0 0 0 0 21 28 1 0 0 0 0 21 38 1 1 0 0 0 22 31 1 0 0 0 0 22 34 1 6 0 0 0 23 32 1 0 0 0 0 23 35 1 0 0 0 0 24 35 1 6 0 0 0 24 39 1 0 0 0 0 25 31 1 0 0 0 0 25 44 1 6 0 0 0 26 33 1 6 0 0 0 27 40 1 1 0 0 0 28 29 1 0 0 0 0 28 41 1 6 0 0 0 29 30 1 0 0 0 0 29 42 1 1 0 0 0 30 43 1 0 0 0 0 30 44 1 6 0 0 0 32 33 1 1 0 0 0 33 7 1 6 0 0 0 34 35 1 1 0 0 0 35 16 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	616.36
Volume:	631.143
LogP:	2.8
LogD:	2.179
LogS:	-4.644
# Rotatable Bonds:	7
TPSA:	150.59
# H-Bond Aceptor:	9
# H-Bond Donor:	4
# Rings:	6
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.25
Synthetic Accessibility Score:	6.465
Fsp3:	0.857
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.083
MDCK Permeability:	1.3254622899694368e-05
Pgp-inhibitor:	0.878
Pgp-substrate:	0.41
Human Intestinal Absorption (HIA):	0.024
20% Bioavailability (F20%):	0.303
30% Bioavailability (F30%):	0.793

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.167
Plasma Protein Binding (PPB):	92.1978988647461%
Volume Distribution (VD):	0.503
Pgp-substrate:	4.901516914367676%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.012
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.066
CYP2C9-substrate:	0.039
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.124
CYP3A4-inhibitor:	0.521
CYP3A4-substrate:	0.278

ADMET: Excretion

Clearance (CL):	2.203
Half-life (T1/2):	0.543

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.27
Drug-inuced Liver Injury (DILI):	0.051
AMES Toxicity:	0.236
Rat Oral Acute Toxicity:	0.738
Maximum Recommended Daily Dose:	0.953
Skin Sensitization:	0.145
Carcinogencity:	0.121
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.571

Download Data

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

Natural Product: NPC472257

Natural Product ID:	NPC472257
*Common Name:**	YLUFIQVDBFZELV-PKQRHZCNSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YLUFIQVDBFZELV-PKQRHZCNSA-N
Standard InCHI:	InChI=1S/C35H52O9/c1-17(2)27(40)19(36)12-18(3)26-20(37)13-32(6)23-9-8-22-31(4,5)25(44-30-29(42)28(41)21(38)15-43-30)10-11-34(22)16-35(23,34)24(39)14-33(26,32)7/h9,18,21-22,24-30,38-42H,1,8,10-16H2,2-7H3/t18-,21-,22+,24+,25+,26+,27-,28+,29-,30+,32+,33-,34-,35-/m1/s1
SMILES:	O[C@@H](C(=O)C[C@H]([C@H]1C(=O)C[C@@]2([C@]1(C)C[C@H](O)[C@]13C2=CC[C@@H]2[C@]3(C1)CC[C@@H](C2(C)C)O[C@@H]1OC[C@H]([C@@H]([C@H]1O)O)O)C)C)C(=C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3355567
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	aerial part	n.a.	PMID[19280146]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	rhizomes	n.a.	n.a.	PMID[25136911]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO31564	Cimicifuga foetida	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

☑ 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	2
NON-MOLECULAR	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT83	Cell Line	MCF7	Homo sapiens	IC50	>	10000.0	nM	PMID[453302]
NPT165	Cell Line	HeLa	Homo sapiens	IC50	>	10000.0	nM	PMID[453302]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[453302]

☑ 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 NPC472257 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	260
0.1-0.2	1639
0.2-0.3	4997
0.3-0.4	10129
0.4-0.5	11272
0.5-0.6	6584
0.6-0.7	4878
0.7-0.8	2761
0.8-0.85	158
0.85-0.9	17
0.9-0.95	1
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9018	High Similarity	NPC130427
0.886	High Similarity	NPC474557
0.8839	High Similarity	NPC475317
0.8839	High Similarity	NPC154856
0.8839	High Similarity	NPC52241
0.8729	High Similarity	NPC202051
0.8684	High Similarity	NPC210420
0.8684	High Similarity	NPC474265
0.8655	High Similarity	NPC28532
0.8649	High Similarity	NPC210178
0.8644	High Similarity	NPC129393
0.8644	High Similarity	NPC472076
0.8644	High Similarity	NPC472075
0.8644	High Similarity	NPC471406
0.8609	High Similarity	NPC260665
0.8596	High Similarity	NPC263827
0.8596	High Similarity	NPC285410
0.8596	High Similarity	NPC250481
0.8584	High Similarity	NPC118225
0.8584	High Similarity	NPC246205
0.8584	High Similarity	NPC265655
0.8583	High Similarity	NPC472077
0.8583	High Similarity	NPC472078
0.8534	High Similarity	NPC473882
0.8534	High Similarity	NPC116024
0.8534	High Similarity	NPC220293
0.8534	High Similarity	NPC472274
0.8534	High Similarity	NPC74727
0.8512	High Similarity	NPC475194
0.8509	High Similarity	NPC129340
0.8496	Intermediate Similarity	NPC195708
0.8496	Intermediate Similarity	NPC295389
0.8475	Intermediate Similarity	NPC239293
0.8462	Intermediate Similarity	NPC279638
0.8448	Intermediate Similarity	NPC293038
0.8448	Intermediate Similarity	NPC251309
0.8448	Intermediate Similarity	NPC62696
0.8435	Intermediate Similarity	NPC269466
0.8435	Intermediate Similarity	NPC292196
0.8403	Intermediate Similarity	NPC161738
0.84	Intermediate Similarity	NPC471855
0.8393	Intermediate Similarity	NPC75608
0.839	Intermediate Similarity	NPC309433
0.8376	Intermediate Similarity	NPC102088
0.8376	Intermediate Similarity	NPC469877
0.8376	Intermediate Similarity	NPC470919
0.8362	Intermediate Similarity	NPC302146
0.8362	Intermediate Similarity	NPC233003
0.8362	Intermediate Similarity	NPC174836
0.8361	Intermediate Similarity	NPC130229
0.8361	Intermediate Similarity	NPC318135
0.8319	Intermediate Similarity	NPC162033
0.8319	Intermediate Similarity	NPC45475
0.8306	Intermediate Similarity	NPC69273
0.8306	Intermediate Similarity	NPC168899
0.8306	Intermediate Similarity	NPC293623
0.8305	Intermediate Similarity	NPC244127
0.8305	Intermediate Similarity	NPC259306
0.8305	Intermediate Similarity	NPC470628
0.8305	Intermediate Similarity	NPC474046
0.8304	Intermediate Similarity	NPC473198
0.8295	Intermediate Similarity	NPC477232
0.8295	Intermediate Similarity	NPC477233
0.8293	Intermediate Similarity	NPC47113
0.8293	Intermediate Similarity	NPC174367
0.8291	Intermediate Similarity	NPC51978
0.8264	Intermediate Similarity	NPC476544
0.8264	Intermediate Similarity	NPC476545
0.8264	Intermediate Similarity	NPC249553
0.8264	Intermediate Similarity	NPC476543
0.8264	Intermediate Similarity	NPC182900
0.8261	Intermediate Similarity	NPC477070
0.8261	Intermediate Similarity	NPC477069
0.8254	Intermediate Similarity	NPC473519
0.8254	Intermediate Similarity	NPC473805
0.825	Intermediate Similarity	NPC190939
0.825	Intermediate Similarity	NPC122971
0.825	Intermediate Similarity	NPC197003
0.825	Intermediate Similarity	NPC477071
0.824	Intermediate Similarity	NPC471407
0.823	Intermediate Similarity	NPC149124
0.823	Intermediate Similarity	NPC223741
0.823	Intermediate Similarity	NPC75531
0.8226	Intermediate Similarity	NPC152091
0.822	Intermediate Similarity	NPC475163
0.822	Intermediate Similarity	NPC165439
0.822	Intermediate Similarity	NPC475633
0.822	Intermediate Similarity	NPC181145
0.822	Intermediate Similarity	NPC474906
0.822	Intermediate Similarity	NPC18547
0.8211	Intermediate Similarity	NPC30188
0.8211	Intermediate Similarity	NPC177820
0.8205	Intermediate Similarity	NPC289312
0.8205	Intermediate Similarity	NPC11252
0.8197	Intermediate Similarity	NPC216866
0.8197	Intermediate Similarity	NPC94072
0.8197	Intermediate Similarity	NPC305771
0.8197	Intermediate Similarity	NPC15918
0.8197	Intermediate Similarity	NPC169816
0.819	Intermediate Similarity	NPC83005
0.819	Intermediate Similarity	NPC101450
0.819	Intermediate Similarity	NPC470065
0.819	Intermediate Similarity	NPC274507
0.8189	Intermediate Similarity	NPC475487
0.8189	Intermediate Similarity	NPC102015
0.8175	Intermediate Similarity	NPC173347
0.8175	Intermediate Similarity	NPC241008
0.8174	Intermediate Similarity	NPC272576
0.8174	Intermediate Similarity	NPC28198
0.8174	Intermediate Similarity	NPC177246
0.8174	Intermediate Similarity	NPC284807
0.8174	Intermediate Similarity	NPC476123
0.8167	Intermediate Similarity	NPC473617
0.8167	Intermediate Similarity	NPC473828
0.8167	Intermediate Similarity	NPC475632
0.8167	Intermediate Similarity	NPC86020
0.8167	Intermediate Similarity	NPC286347
0.816	Intermediate Similarity	NPC245094
0.816	Intermediate Similarity	NPC311534
0.8158	Intermediate Similarity	NPC472898
0.8158	Intermediate Similarity	NPC95243
0.8158	Intermediate Similarity	NPC165405
0.8158	Intermediate Similarity	NPC472899
0.8158	Intermediate Similarity	NPC472900
0.8158	Intermediate Similarity	NPC63023
0.8151	Intermediate Similarity	NPC235539
0.8151	Intermediate Similarity	NPC134869
0.8151	Intermediate Similarity	NPC152199
0.8151	Intermediate Similarity	NPC31797
0.8145	Intermediate Similarity	NPC476673
0.8136	Intermediate Similarity	NPC477944
0.8136	Intermediate Similarity	NPC311592
0.8136	Intermediate Similarity	NPC75167
0.8136	Intermediate Similarity	NPC73986
0.813	Intermediate Similarity	NPC476542
0.8125	Intermediate Similarity	NPC470434
0.812	Intermediate Similarity	NPC477073
0.812	Intermediate Similarity	NPC471243
0.812	Intermediate Similarity	NPC297208
0.812	Intermediate Similarity	NPC201992
0.812	Intermediate Similarity	NPC191763
0.812	Intermediate Similarity	NPC30397
0.812	Intermediate Similarity	NPC235841
0.812	Intermediate Similarity	NPC211798
0.812	Intermediate Similarity	NPC473481
0.812	Intermediate Similarity	NPC108748
0.8115	Intermediate Similarity	NPC75417
0.8115	Intermediate Similarity	NPC476672
0.8115	Intermediate Similarity	NPC42675
0.8115	Intermediate Similarity	NPC475182
0.8115	Intermediate Similarity	NPC476675
0.811	Intermediate Similarity	NPC231240
0.8103	Intermediate Similarity	NPC204407
0.8103	Intermediate Similarity	NPC127853
0.8103	Intermediate Similarity	NPC57362
0.8103	Intermediate Similarity	NPC8431
0.8103	Intermediate Similarity	NPC306746
0.8103	Intermediate Similarity	NPC167383
0.8103	Intermediate Similarity	NPC143706
0.8103	Intermediate Similarity	NPC237503
0.8103	Intermediate Similarity	NPC137917
0.8103	Intermediate Similarity	NPC472534
0.8099	Intermediate Similarity	NPC6377
0.8099	Intermediate Similarity	NPC475171
0.8099	Intermediate Similarity	NPC469945
0.8099	Intermediate Similarity	NPC157868
0.8099	Intermediate Similarity	NPC476529
0.8099	Intermediate Similarity	NPC39211
0.8099	Intermediate Similarity	NPC475775
0.8099	Intermediate Similarity	NPC114441
0.8099	Intermediate Similarity	NPC35405
0.8099	Intermediate Similarity	NPC11551
0.8099	Intermediate Similarity	NPC473884
0.8099	Intermediate Similarity	NPC192791
0.8099	Intermediate Similarity	NPC208381
0.8099	Intermediate Similarity	NPC472949
0.8099	Intermediate Similarity	NPC319570
0.8099	Intermediate Similarity	NPC180550
0.8099	Intermediate Similarity	NPC214484
0.8099	Intermediate Similarity	NPC309780
0.8087	Intermediate Similarity	NPC293512
0.8087	Intermediate Similarity	NPC473538
0.8087	Intermediate Similarity	NPC283849
0.8083	Intermediate Similarity	NPC224121
0.8083	Intermediate Similarity	NPC477252
0.808	Intermediate Similarity	NPC42399
0.807	Intermediate Similarity	NPC221562
0.807	Intermediate Similarity	NPC470885
0.807	Intermediate Similarity	NPC121566
0.807	Intermediate Similarity	NPC93352
0.807	Intermediate Similarity	NPC100955
0.807	Intermediate Similarity	NPC187400
0.8067	Intermediate Similarity	NPC477580
0.8065	Intermediate Similarity	NPC248202
0.8065	Intermediate Similarity	NPC473505
0.8065	Intermediate Similarity	NPC470477
0.8053	Intermediate Similarity	NPC136816
0.8051	Intermediate Similarity	NPC46388
0.8051	Intermediate Similarity	NPC116794
0.8051	Intermediate Similarity	NPC280782

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 NPC472257 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	225
0.1-0.2	1856
0.2-0.3	4020
0.3-0.4	2000
0.4-0.5	558
0.5-0.6	265
0.6-0.7	143
0.7-0.8	82
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8087	Intermediate Similarity	NPD6412	Phase 2
0.7984	Intermediate Similarity	NPD8328	Phase 3
0.7934	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7903	Intermediate Similarity	NPD6370	Approved
0.7874	Intermediate Similarity	NPD7736	Approved
0.7857	Intermediate Similarity	NPD7507	Approved
0.7797	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7795	Intermediate Similarity	NPD8293	Discontinued
0.775	Intermediate Similarity	NPD8297	Approved
0.775	Intermediate Similarity	NPD6882	Approved
0.7742	Intermediate Similarity	NPD6054	Approved
0.7742	Intermediate Similarity	NPD6059	Approved
0.7674	Intermediate Similarity	NPD7319	Approved
0.7542	Intermediate Similarity	NPD5739	Approved
0.7542	Intermediate Similarity	NPD6675	Approved
0.7542	Intermediate Similarity	NPD6402	Approved
0.7542	Intermediate Similarity	NPD7128	Approved
0.7541	Intermediate Similarity	NPD8133	Approved
0.754	Intermediate Similarity	NPD6016	Approved
0.754	Intermediate Similarity	NPD6015	Approved
0.75	Intermediate Similarity	NPD7492	Approved
0.75	Intermediate Similarity	NPD6373	Approved
0.75	Intermediate Similarity	NPD6009	Approved
0.75	Intermediate Similarity	NPD6372	Approved
0.748	Intermediate Similarity	NPD5988	Approved
0.746	Intermediate Similarity	NPD6319	Approved
0.7442	Intermediate Similarity	NPD6616	Approved
0.7436	Intermediate Similarity	NPD5211	Phase 2
0.7417	Intermediate Similarity	NPD7320	Approved
0.7417	Intermediate Similarity	NPD6686	Approved
0.7417	Intermediate Similarity	NPD6881	Approved
0.7417	Intermediate Similarity	NPD6899	Approved
0.7402	Intermediate Similarity	NPD8033	Approved
0.7398	Intermediate Similarity	NPD4632	Approved
0.7391	Intermediate Similarity	NPD4755	Approved
0.7385	Intermediate Similarity	NPD7078	Approved
0.7377	Intermediate Similarity	NPD6650	Approved
0.7377	Intermediate Similarity	NPD6649	Approved
0.7377	Intermediate Similarity	NPD8130	Phase 1
0.736	Intermediate Similarity	NPD7115	Discovery
0.7333	Intermediate Similarity	NPD5701	Approved
0.7333	Intermediate Similarity	NPD5697	Approved
0.7323	Intermediate Similarity	NPD8294	Approved
0.7323	Intermediate Similarity	NPD8377	Approved
0.7311	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7311	Intermediate Similarity	NPD5141	Approved
0.7302	Intermediate Similarity	NPD7327	Approved
0.7302	Intermediate Similarity	NPD7328	Approved
0.7295	Intermediate Similarity	NPD7290	Approved
0.7295	Intermediate Similarity	NPD7102	Approved
0.7295	Intermediate Similarity	NPD6883	Approved
0.7287	Intermediate Similarity	NPD7604	Phase 2
0.7266	Intermediate Similarity	NPD8516	Approved
0.7266	Intermediate Similarity	NPD8296	Approved
0.7266	Intermediate Similarity	NPD8515	Approved
0.7266	Intermediate Similarity	NPD8513	Phase 3
0.7266	Intermediate Similarity	NPD8380	Approved
0.7266	Intermediate Similarity	NPD8379	Approved
0.7266	Intermediate Similarity	NPD8335	Approved
0.7266	Intermediate Similarity	NPD8517	Approved
0.7266	Intermediate Similarity	NPD8378	Approved
0.7265	Intermediate Similarity	NPD5286	Approved
0.7265	Intermediate Similarity	NPD4700	Approved
0.7265	Intermediate Similarity	NPD4696	Approved
0.7265	Intermediate Similarity	NPD5285	Approved
0.7244	Intermediate Similarity	NPD7516	Approved
0.7236	Intermediate Similarity	NPD6617	Approved
0.7236	Intermediate Similarity	NPD6869	Approved
0.7236	Intermediate Similarity	NPD6847	Approved
0.7232	Intermediate Similarity	NPD5328	Approved
0.7213	Intermediate Similarity	NPD6012	Approved
0.7213	Intermediate Similarity	NPD6013	Approved
0.7213	Intermediate Similarity	NPD6014	Approved
0.7197	Intermediate Similarity	NPD6033	Approved
0.7193	Intermediate Similarity	NPD6399	Phase 3
0.7155	Intermediate Similarity	NPD5221	Approved
0.7155	Intermediate Similarity	NPD5222	Approved
0.7155	Intermediate Similarity	NPD4697	Phase 3
0.7155	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD4634	Approved
0.7143	Intermediate Similarity	NPD5224	Approved
0.7143	Intermediate Similarity	NPD5225	Approved
0.7143	Intermediate Similarity	NPD5226	Approved
0.7143	Intermediate Similarity	NPD4633	Approved
0.7132	Intermediate Similarity	NPD7503	Approved
0.7131	Intermediate Similarity	NPD6011	Approved
0.7107	Intermediate Similarity	NPD4767	Approved
0.7107	Intermediate Similarity	NPD4768	Approved
0.7105	Intermediate Similarity	NPD6079	Approved
0.7097	Intermediate Similarity	NPD6401	Clinical (unspecified phase)
0.7094	Intermediate Similarity	NPD5173	Approved
0.7091	Intermediate Similarity	NPD4786	Approved
0.7083	Intermediate Similarity	NPD5175	Approved
0.7083	Intermediate Similarity	NPD5174	Approved
0.7059	Intermediate Similarity	NPD5223	Approved
0.7023	Intermediate Similarity	NPD6067	Discontinued
0.7	Intermediate Similarity	NPD5983	Phase 2
0.6992	Remote Similarity	NPD4730	Approved
0.6992	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4729	Approved
0.6967	Remote Similarity	NPD6008	Approved
0.6949	Remote Similarity	NPD6084	Phase 2
0.6949	Remote Similarity	NPD6083	Phase 2
0.6942	Remote Similarity	NPD4754	Approved
0.6917	Remote Similarity	NPD6336	Discontinued
0.6909	Remote Similarity	NPD3667	Approved
0.6891	Remote Similarity	NPD5696	Approved
0.688	Remote Similarity	NPD5250	Approved
0.688	Remote Similarity	NPD5251	Approved
0.688	Remote Similarity	NPD5248	Approved
0.688	Remote Similarity	NPD5249	Phase 3
0.688	Remote Similarity	NPD5247	Approved
0.6875	Remote Similarity	NPD6274	Approved
0.6855	Remote Similarity	NPD5128	Approved
0.6846	Remote Similarity	NPD7100	Approved
0.6846	Remote Similarity	NPD7101	Approved
0.6838	Remote Similarity	NPD7748	Approved
0.6833	Remote Similarity	NPD7640	Approved
0.6833	Remote Similarity	NPD7639	Approved
0.6825	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD3618	Phase 1
0.681	Remote Similarity	NPD8034	Phase 2
0.681	Remote Similarity	NPD8035	Phase 2
0.6807	Remote Similarity	NPD7902	Approved
0.6783	Remote Similarity	NPD4753	Phase 2
0.678	Remote Similarity	NPD5210	Approved
0.678	Remote Similarity	NPD4629	Approved
0.6769	Remote Similarity	NPD6335	Approved
0.6752	Remote Similarity	NPD4202	Approved
0.675	Remote Similarity	NPD7638	Approved
0.6744	Remote Similarity	NPD6868	Approved
0.6742	Remote Similarity	NPD6908	Approved
0.6742	Remote Similarity	NPD6909	Approved
0.6696	Remote Similarity	NPD5737	Approved
0.6696	Remote Similarity	NPD6672	Approved
0.6693	Remote Similarity	NPD5217	Approved
0.6693	Remote Similarity	NPD5215	Approved
0.6693	Remote Similarity	NPD5216	Approved
0.6692	Remote Similarity	NPD6317	Approved
0.6667	Remote Similarity	NPD7515	Phase 2
0.6667	Remote Similarity	NPD7260	Phase 2
0.6667	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6641	Remote Similarity	NPD6313	Approved
0.6641	Remote Similarity	NPD6314	Approved
0.6639	Remote Similarity	NPD5695	Phase 3
0.6618	Remote Similarity	NPD8074	Phase 3
0.6614	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5135	Approved
0.6614	Remote Similarity	NPD5169	Approved
0.6587	Remote Similarity	NPD5168	Approved
0.6579	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD5127	Approved
0.6555	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6555	Remote Similarity	NPD7900	Approved
0.6525	Remote Similarity	NPD6411	Approved
0.6522	Remote Similarity	NPD5279	Phase 3
0.65	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6493	Remote Similarity	NPD6921	Approved
0.6491	Remote Similarity	NPD3666	Approved
0.6491	Remote Similarity	NPD3665	Phase 1
0.6491	Remote Similarity	NPD3668	Phase 3
0.6491	Remote Similarity	NPD3133	Approved
0.6484	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD5956	Approved
0.6475	Remote Similarity	NPD4225	Approved
0.6471	Remote Similarity	NPD8171	Discontinued
0.6466	Remote Similarity	NPD7524	Approved
0.6449	Remote Similarity	NPD8337	Approved
0.6449	Remote Similarity	NPD8336	Approved
0.6435	Remote Similarity	NPD5329	Approved
0.6429	Remote Similarity	NPD7525	Registered
0.6412	Remote Similarity	NPD5167	Approved
0.641	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6387	Remote Similarity	NPD7983	Approved
0.6385	Remote Similarity	NPD6053	Discontinued
0.6383	Remote Similarity	NPD6845	Suspended
0.6383	Remote Similarity	NPD8449	Approved
0.6383	Remote Similarity	NPD8338	Approved
0.6379	Remote Similarity	NPD6098	Approved
0.6379	Remote Similarity	NPD7334	Approved
0.6379	Remote Similarity	NPD6409	Approved
0.6379	Remote Similarity	NPD7146	Approved
0.6379	Remote Similarity	NPD5330	Approved
0.6379	Remote Similarity	NPD7521	Approved
0.6379	Remote Similarity	NPD6684	Approved
0.6356	Remote Similarity	NPD6673	Approved
0.6356	Remote Similarity	NPD6080	Approved
0.6356	Remote Similarity	NPD6904	Approved
0.6356	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6356	Remote Similarity	NPD6101	Approved
0.6348	Remote Similarity	NPD4197	Approved
0.6348	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6338	Remote Similarity	NPD8450	Suspended
0.6333	Remote Similarity	NPD5779	Approved
0.6333	Remote Similarity	NPD5778	Approved
0.6325	Remote Similarity	NPD3573	Approved
0.632	Remote Similarity	NPD7632	Discontinued
0.6303	Remote Similarity	NPD46	Approved
0.6303	Remote Similarity	NPD6698	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