NPASS Compound

Structure

CID18347 OpenBabel06191715342D 27 32 0 0 1 0 0 0 0 0999 V2000 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 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 0 0 0 0 0 0 0 0 0 0 5.2437 1.0933 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9128 1.8364 0.0000 C 0 0 0 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 4.4347 2.4945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 1.0000 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 0.8660 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 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 0.8286 -0.3252 0.0000 C 0 0 0 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 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.9033 -1.3224 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9947 -0.1026 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4128 2.7024 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 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5994 0.1199 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3 5 1 0 0 0 0 3 10 1 0 0 0 0 4 6 2 0 0 0 0 4 9 1 0 0 0 0 5 19 1 0 0 0 0 6 24 1 0 0 0 0 7 11 1 0 0 0 0 7 18 1 0 0 0 0 8 9 2 0 0 0 0 8 24 1 0 0 0 0 10 16 1 0 0 0 0 10 18 1 6 0 0 0 11 9 1 6 0 0 0 11 25 1 0 0 0 0 12 13 1 0 0 0 0 12 14 1 0 0 0 0 12 27 1 6 0 0 0 13 15 1 0 0 0 0 13 26 1 6 0 0 0 14 18 1 0 0 0 0 14 19 1 6 0 0 0 15 20 1 6 0 0 0 15 26 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 20 1 0 0 0 0 17 22 2 0 0 0 0 17 27 1 0 0 0 0 18 1 1 1 0 0 0 19 2 1 6 0 0 0 20 19 1 1 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	374.14
Volume:	354.123
LogP:	2.568
LogD:	2.423
LogS:	-4.241
# Rotatable Bonds:	1
TPSA:	98.5
# H-Bond Aceptor:	7
# H-Bond Donor:	1
# Rings:	7
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.59
Synthetic Accessibility Score:	5.848
Fsp3:	0.7
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.281
MDCK Permeability:	5.077086461824365e-05
Pgp-inhibitor:	0.893
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.049
30% Bioavailability (F30%):	0.842

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.803
Plasma Protein Binding (PPB):	87.0527572631836%
Volume Distribution (VD):	2.134
Pgp-substrate:	18.365280151367188%

ADMET: Metabolism

CYP1A2-inhibitor:	0.086
CYP1A2-substrate:	0.52
CYP2C19-inhibitor:	0.159
CYP2C19-substrate:	0.429
CYP2C9-inhibitor:	0.035
CYP2C9-substrate:	0.025
CYP2D6-inhibitor:	0.012
CYP2D6-substrate:	0.173
CYP3A4-inhibitor:	0.905
CYP3A4-substrate:	0.286

ADMET: Excretion

Clearance (CL):	13.655
Half-life (T1/2):	0.069

ADMET: Toxicity

hERG Blockers:	0.044
Human Hepatotoxicity (H-HT):	0.332
Drug-inuced Liver Injury (DILI):	0.487
AMES Toxicity:	0.095
Rat Oral Acute Toxicity:	0.959
Maximum Recommended Daily Dose:	0.813
Skin Sensitization:	0.211
Carcinogencity:	0.666
Eye Corrosion:	0.081
Eye Irritation:	0.059
Respiratory Toxicity:	0.968

Download Data

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

Natural Product: NPC18347

Natural Product ID:	NPC18347
*Common Name:**	Chasmanthin
IUPAC Name:	n.a.
Synonyms:	Chasmanthin
Standard InCHIKey:	TXOMRNMZLZXJQP-OQDMGONLSA-N
Standard InCHI:	InChI=1S/C20H22O7/c1-18-7-11(9-4-6-24-8-9)25-16(21)10(18)3-5-19(2)14(18)12-13-15(26-13)20(19,23)17(22)27-12/h4,6,8,10-15,23H,3,5,7H2,1-2H3/t10-,11+,12+,13-,14-,15-,18+,19+,20-/m0/s1
SMILES:	O=C1O[C@H](C[C@@]2([C@H]1CC[C@@]1([C@H]2[C@@H]2OC(=O)[C@@]1(O)[C@@H]1[C@H]2O1)C)C)c1cocc1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL458613
PubChem CID:	442012
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17994701]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18829331]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19568	Aconitum chrysotrichum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19568	Aconitum chrysotrichum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19929	Jateorhiza palmata	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10715	Fibraurea tinctoria	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19568	Aconitum chrysotrichum	Species	Ranunculaceae	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
Others	12

Activity Type	# Activity
Organism	12

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.39	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.46	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	22.41	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.99	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	31.6	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	32.49	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	13.15	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	18.75	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.76	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	21.23	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	23.73	%	PMID[491848]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	20.71	%	PMID[491848]

☑ 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 NPC18347 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	398
0.1-0.2	1562
0.2-0.3	3524
0.3-0.4	6167
0.4-0.5	10187
0.5-0.6	9964
0.6-0.7	9024
0.7-0.8	1567
0.8-0.85	180
0.85-0.9	89
0.9-0.95	32
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9869	High Similarity	NPC271657
0.9868	High Similarity	NPC149896
0.9416	High Similarity	NPC299038
0.9416	High Similarity	NPC187149
0.9379	High Similarity	NPC262386
0.9367	High Similarity	NPC173516
0.9359	High Similarity	NPC200782
0.9359	High Similarity	NPC82851
0.9355	High Similarity	NPC475967
0.9308	High Similarity	NPC471397
0.9308	High Similarity	NPC271235
0.9308	High Similarity	NPC160651
0.9299	High Similarity	NPC134254
0.9299	High Similarity	NPC302369
0.9299	High Similarity	NPC234660
0.9299	High Similarity	NPC51568
0.9299	High Similarity	NPC39986
0.9295	High Similarity	NPC335761
0.9295	High Similarity	NPC472653
0.929	High Similarity	NPC261597
0.9286	High Similarity	NPC44675
0.9286	High Similarity	NPC214541
0.9236	High Similarity	NPC5079
0.9177	High Similarity	NPC292389
0.9177	High Similarity	NPC477405
0.9177	High Similarity	NPC469338
0.9167	High Similarity	NPC45101
0.9167	High Similarity	NPC249021
0.9167	High Similarity	NPC36655
0.9161	High Similarity	NPC476262
0.9156	High Similarity	NPC476201
0.9156	High Similarity	NPC268905
0.9156	High Similarity	NPC44577
0.9125	High Similarity	NPC472774
0.9125	High Similarity	NPC472775
0.9125	High Similarity	NPC472282
0.9125	High Similarity	NPC472651
0.9119	High Similarity	NPC476856
0.9119	High Similarity	NPC469849
0.9119	High Similarity	NPC276551
0.9119	High Similarity	NPC476860
0.9119	High Similarity	NPC470940
0.9119	High Similarity	NPC476857
0.9119	High Similarity	NPC470182
0.9119	High Similarity	NPC476858
0.9114	High Similarity	NPC117986
0.9108	High Similarity	NPC473473
0.9108	High Similarity	NPC475295
0.9103	High Similarity	NPC209364
0.9103	High Similarity	NPC107646
0.9097	High Similarity	NPC57998
0.9097	High Similarity	NPC282445
0.9068	High Similarity	NPC472652
0.9062	High Similarity	NPC93172
0.9062	High Similarity	NPC97574
0.9062	High Similarity	NPC23387
0.9062	High Similarity	NPC470875
0.9057	High Similarity	NPC469846
0.9051	High Similarity	NPC25255
0.9045	High Similarity	NPC286722
0.9026	High Similarity	NPC476122
0.9012	High Similarity	NPC82602
0.9006	High Similarity	NPC476861
0.9006	High Similarity	NPC476850
0.9006	High Similarity	NPC476853
0.8994	High Similarity	NPC193798
0.8994	High Similarity	NPC96443
0.8994	High Similarity	NPC470939
0.8994	High Similarity	NPC69028
0.8994	High Similarity	NPC290400
0.8981	High Similarity	NPC126723
0.8981	High Similarity	NPC60973
0.8961	High Similarity	NPC69647
0.8961	High Similarity	NPC125182
0.8957	High Similarity	NPC169299
0.8957	High Similarity	NPC160818
0.8954	High Similarity	NPC255414
0.8938	High Similarity	NPC472773
0.8931	High Similarity	NPC477402
0.8931	High Similarity	NPC305016
0.8931	High Similarity	NPC475381
0.8917	High Similarity	NPC264943
0.891	High Similarity	NPC469503
0.8896	High Similarity	NPC470995
0.8882	High Similarity	NPC123088
0.8875	High Similarity	NPC211777
0.8875	High Similarity	NPC329938
0.8875	High Similarity	NPC472771
0.8875	High Similarity	NPC263432
0.8868	High Similarity	NPC477403
0.8861	High Similarity	NPC263265
0.8846	High Similarity	NPC18135
0.8827	High Similarity	NPC472141
0.882	High Similarity	NPC476197
0.882	High Similarity	NPC198047
0.882	High Similarity	NPC472139
0.8805	High Similarity	NPC472778
0.8805	High Similarity	NPC472777
0.8805	High Similarity	NPC472776
0.8782	High Similarity	NPC477404
0.8782	High Similarity	NPC196864
0.8765	High Similarity	NPC146991
0.8758	High Similarity	NPC86935
0.8758	High Similarity	NPC207978
0.8758	High Similarity	NPC188649
0.875	High Similarity	NPC237155
0.8742	High Similarity	NPC469485
0.8735	High Similarity	NPC236004
0.8735	High Similarity	NPC94763
0.8734	High Similarity	NPC178932
0.872	High Similarity	NPC296558
0.871	High Similarity	NPC470941
0.871	High Similarity	NPC221809
0.8704	High Similarity	NPC419
0.8704	High Similarity	NPC88841
0.8704	High Similarity	NPC288602
0.8701	High Similarity	NPC5676
0.8688	High Similarity	NPC472283
0.8688	High Similarity	NPC167142
0.8688	High Similarity	NPC472772
0.8688	High Similarity	NPC173544
0.8679	High Similarity	NPC469850
0.8679	High Similarity	NPC469336
0.8671	High Similarity	NPC75906
0.8659	High Similarity	NPC473766
0.8659	High Similarity	NPC473753
0.8659	High Similarity	NPC100333
0.8645	High Similarity	NPC346
0.8642	High Similarity	NPC18986
0.8639	High Similarity	NPC470938
0.8636	High Similarity	NPC137295
0.8636	High Similarity	NPC476944
0.8636	High Similarity	NPC251865
0.8634	High Similarity	NPC262872
0.8634	High Similarity	NPC307383
0.8631	High Similarity	NPC478177
0.8631	High Similarity	NPC472665
0.8627	High Similarity	NPC121158
0.8616	High Similarity	NPC30222
0.8614	High Similarity	NPC159232
0.8599	High Similarity	NPC195325
0.8598	High Similarity	NPC478178
0.8598	High Similarity	NPC121995
0.859	High Similarity	NPC250228
0.858	High Similarity	NPC287559
0.858	High Similarity	NPC470789
0.8571	High Similarity	NPC194499
0.8571	High Similarity	NPC195954
0.8571	High Similarity	NPC243577
0.8571	High Similarity	NPC88007
0.8562	High Similarity	NPC35000
0.8562	High Similarity	NPC281258
0.8554	High Similarity	NPC472659
0.8554	High Similarity	NPC302392
0.8553	High Similarity	NPC147168
0.8544	High Similarity	NPC159927
0.8544	High Similarity	NPC469335
0.8537	High Similarity	NPC56358
0.8528	High Similarity	NPC68848
0.8528	High Similarity	NPC472668
0.8519	High Similarity	NPC474611
0.8519	High Similarity	NPC475226
0.8519	High Similarity	NPC473368
0.8512	High Similarity	NPC469576
0.85	High Similarity	NPC114880
0.8497	Intermediate Similarity	NPC90296
0.8494	Intermediate Similarity	NPC472766
0.8494	Intermediate Similarity	NPC327922
0.8494	Intermediate Similarity	NPC472765
0.8488	Intermediate Similarity	NPC247563
0.8488	Intermediate Similarity	NPC105395
0.8488	Intermediate Similarity	NPC242068
0.8485	Intermediate Similarity	NPC475779
0.8481	Intermediate Similarity	NPC472654
0.8481	Intermediate Similarity	NPC211625
0.8476	Intermediate Similarity	NPC285567
0.8476	Intermediate Similarity	NPC283209
0.8476	Intermediate Similarity	NPC224394
0.8476	Intermediate Similarity	NPC165218
0.8476	Intermediate Similarity	NPC663
0.8476	Intermediate Similarity	NPC472669
0.8466	Intermediate Similarity	NPC8389
0.8462	Intermediate Similarity	NPC469633
0.8462	Intermediate Similarity	NPC41182
0.8452	Intermediate Similarity	NPC476946
0.8434	Intermediate Similarity	NPC472764
0.8434	Intermediate Similarity	NPC478179
0.8434	Intermediate Similarity	NPC270312
0.8428	Intermediate Similarity	NPC228842
0.8424	Intermediate Similarity	NPC259943
0.8421	Intermediate Similarity	NPC310830
0.8418	Intermediate Similarity	NPC19747
0.8415	Intermediate Similarity	NPC470792
0.8415	Intermediate Similarity	NPC79571
0.8415	Intermediate Similarity	NPC471166
0.8415	Intermediate Similarity	NPC471167
0.8408	Intermediate Similarity	NPC262198
0.8402	Intermediate Similarity	NPC471437
0.8402	Intermediate Similarity	NPC471632
0.8393	Intermediate Similarity	NPC294512

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 NPC18347 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	337
0.1-0.2	1095
0.2-0.3	2279
0.3-0.4	2717
0.4-0.5	1749
0.5-0.6	724
0.6-0.7	233
0.7-0.8	16
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
0.8324	Intermediate Similarity	NPD8434	Phase 2
0.8221	Intermediate Similarity	NPD5760	Phase 2
0.8221	Intermediate Similarity	NPD5761	Phase 2
0.7811	Intermediate Similarity	NPD5537	Clinical (unspecified phase)
0.7574	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7558	Intermediate Similarity	NPD5494	Approved
0.7528	Intermediate Similarity	NPD6765	Approved
0.7528	Intermediate Similarity	NPD6764	Approved
0.75	Intermediate Similarity	NPD6599	Discontinued
0.7442	Intermediate Similarity	NPD7075	Discontinued
0.7378	Intermediate Similarity	NPD4628	Phase 3
0.7363	Intermediate Similarity	NPD6784	Approved
0.7363	Intermediate Similarity	NPD6785	Approved
0.7363	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD5844	Phase 1
0.7333	Intermediate Similarity	NPD6559	Discontinued
0.7303	Intermediate Similarity	NPD3751	Discontinued
0.7299	Intermediate Similarity	NPD919	Approved
0.7283	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3787	Discontinued
0.7267	Intermediate Similarity	NPD7819	Suspended
0.7258	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6799	Approved
0.7241	Intermediate Similarity	NPD3749	Approved
0.7236	Intermediate Similarity	NPD8404	Phase 2
0.7225	Intermediate Similarity	NPD3817	Phase 2
0.7225	Intermediate Similarity	NPD5402	Approved
0.7219	Intermediate Similarity	NPD920	Approved
0.7216	Intermediate Similarity	NPD1247	Approved
0.7209	Intermediate Similarity	NPD6801	Discontinued
0.7191	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD6166	Phase 2
0.7184	Intermediate Similarity	NPD3882	Suspended
0.7168	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD1934	Approved
0.7104	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2533	Approved
0.7101	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD2532	Approved
0.7101	Intermediate Similarity	NPD2534	Approved
0.7093	Intermediate Similarity	NPD4380	Phase 2
0.7088	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.7072	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7066	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7052	Intermediate Similarity	NPD7411	Suspended
0.7045	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7043	Intermediate Similarity	NPD8150	Discontinued
0.7033	Intermediate Similarity	NPD7074	Phase 3
0.7018	Intermediate Similarity	NPD5403	Approved
0.7017	Intermediate Similarity	NPD3818	Discontinued
0.7	Intermediate Similarity	NPD5401	Approved
0.7	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.6995	Remote Similarity	NPD6797	Phase 2
0.6995	Remote Similarity	NPD4111	Phase 1
0.6988	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD6232	Discontinued
0.6982	Remote Similarity	NPD643	Clinical (unspecified phase)
0.6973	Remote Similarity	NPD8313	Approved
0.6973	Remote Similarity	NPD8312	Approved
0.6971	Remote Similarity	NPD2801	Approved
0.6971	Remote Similarity	NPD1465	Phase 2
0.6961	Remote Similarity	NPD7473	Discontinued
0.6959	Remote Similarity	NPD6273	Approved
0.6957	Remote Similarity	NPD7251	Discontinued
0.6932	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6927	Remote Similarity	NPD8127	Discontinued
0.6927	Remote Similarity	NPD6959	Discontinued
0.6919	Remote Similarity	NPD7808	Phase 3
0.6912	Remote Similarity	NPD4665	Approved
0.6888	Remote Similarity	NPD7435	Discontinued
0.6886	Remote Similarity	NPD2346	Discontinued
0.6886	Remote Similarity	NPD1471	Phase 3
0.6885	Remote Similarity	NPD7054	Approved
0.6865	Remote Similarity	NPD7685	Pre-registration
0.6851	Remote Similarity	NPD7184	Clinical (unspecified phase)
0.6851	Remote Similarity	NPD3926	Phase 2
0.6848	Remote Similarity	NPD7472	Approved
0.6845	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD7907	Approved
0.6845	Remote Similarity	NPD1549	Phase 2
0.6845	Remote Similarity	NPD8407	Phase 2
0.6839	Remote Similarity	NPD3226	Approved
0.6839	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD7228	Approved
0.6826	Remote Similarity	NPD1551	Phase 2
0.6826	Remote Similarity	NPD2796	Approved
0.6821	Remote Similarity	NPD6782	Approved
0.6821	Remote Similarity	NPD6777	Approved
0.6821	Remote Similarity	NPD6781	Approved
0.6821	Remote Similarity	NPD6780	Approved
0.6821	Remote Similarity	NPD6778	Approved
0.6821	Remote Similarity	NPD6779	Approved
0.6821	Remote Similarity	NPD6776	Approved
0.6818	Remote Similarity	NPD37	Approved
0.6816	Remote Similarity	NPD6234	Discontinued
0.6813	Remote Similarity	NPD7852	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD2800	Approved
0.6805	Remote Similarity	NPD1243	Approved
0.6805	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD7497	Discontinued
0.6798	Remote Similarity	NPD4967	Phase 2
0.6798	Remote Similarity	NPD4965	Approved
0.6798	Remote Similarity	NPD7768	Phase 2
0.6798	Remote Similarity	NPD4966	Approved
0.6788	Remote Similarity	NPD6355	Discontinued
0.6786	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD7236	Approved
0.6779	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD8368	Discontinued
0.6766	Remote Similarity	NPD2799	Discontinued
0.6765	Remote Similarity	NPD3750	Approved
0.6763	Remote Similarity	NPD1512	Approved
0.6743	Remote Similarity	NPD7458	Discontinued
0.674	Remote Similarity	NPD7199	Phase 2
0.6739	Remote Similarity	NPD7799	Discontinued
0.6735	Remote Similarity	NPD4107	Approved
0.6726	Remote Similarity	NPD6100	Approved
0.6726	Remote Similarity	NPD6099	Approved
0.6726	Remote Similarity	NPD2935	Discontinued
0.6725	Remote Similarity	NPD6190	Approved
0.6717	Remote Similarity	NPD7698	Approved
0.6717	Remote Similarity	NPD7696	Phase 3
0.6717	Remote Similarity	NPD7697	Approved
0.6705	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5710	Approved
0.6703	Remote Similarity	NPD5711	Approved
0.6702	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD447	Suspended
0.6684	Remote Similarity	NPD7240	Approved
0.6683	Remote Similarity	NPD8320	Phase 1
0.6683	Remote Similarity	NPD8319	Approved
0.6683	Remote Similarity	NPD7874	Approved
0.6683	Remote Similarity	NPD7875	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3748	Approved
0.6667	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7033	Discontinued
0.6667	Remote Similarity	NPD3057	Approved
0.6667	Remote Similarity	NPD6233	Phase 2
0.6667	Remote Similarity	NPD7701	Phase 2
0.665	Remote Similarity	NPD7783	Phase 2
0.665	Remote Similarity	NPD7782	Clinical (unspecified phase)
0.6647	Remote Similarity	NPD1511	Approved
0.6629	Remote Similarity	NPD6980	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD4482	Phase 3
0.6615	Remote Similarity	NPD8360	Approved
0.6615	Remote Similarity	NPD8435	Approved
0.6615	Remote Similarity	NPD8361	Approved
0.6613	Remote Similarity	NPD8470	Clinical (unspecified phase)
0.6612	Remote Similarity	NPD7229	Phase 3
0.6606	Remote Similarity	NPD6859	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD6798	Discontinued
0.6606	Remote Similarity	NPD2313	Discontinued
0.6606	Remote Similarity	NPD1699	Clinical (unspecified phase)
0.66	Remote Similarity	NPD7870	Phase 2
0.66	Remote Similarity	NPD7871	Phase 2
0.6592	Remote Similarity	NPD8455	Phase 2
0.6591	Remote Similarity	NPD7239	Suspended
0.6588	Remote Similarity	NPD2344	Approved
0.6588	Remote Similarity	NPD5762	Approved
0.6588	Remote Similarity	NPD5763	Approved
0.6587	Remote Similarity	NPD230	Phase 1
0.6583	Remote Similarity	NPD2972	Approved
0.6583	Remote Similarity	NPD3533	Approved
0.657	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.657	Remote Similarity	NPD4110	Phase 3
0.657	Remote Similarity	NPD7003	Approved
0.6569	Remote Similarity	NPD7801	Approved
0.6568	Remote Similarity	NPD1510	Phase 2
0.6566	Remote Similarity	NPD4580	Approved
0.6564	Remote Similarity	NPD6534	Approved
0.6564	Remote Similarity	NPD6535	Approved
0.6559	Remote Similarity	NPD7893	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6143	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD7700	Phase 2
0.6548	Remote Similarity	NPD7699	Phase 2
0.6545	Remote Similarity	NPD7095	Approved
0.6541	Remote Similarity	NPD2403	Approved
0.6527	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD1608	Approved
0.6517	Remote Similarity	NPD4582	Approved
0.6517	Remote Similarity	NPD4583	Approved
0.6515	Remote Similarity	NPD8285	Discontinued
0.6514	Remote Similarity	NPD7048	Phase 3
0.6509	Remote Similarity	NPD7097	Phase 1
0.6506	Remote Similarity	NPD3764	Approved
0.65	Remote Similarity	NPD2491	Approved
0.6497	Remote Similarity	NPD2973	Approved
0.6497	Remote Similarity	NPD2975	Approved
0.6497	Remote Similarity	NPD2974	Approved
0.6491	Remote Similarity	NPD6002	Phase 3
0.6491	Remote Similarity	NPD6005	Phase 3
0.6491	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6491	Remote Similarity	NPD6004	Phase 3
0.6491	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5124	Phase 1
0.6488	Remote Similarity	NPD5676	Approved
0.6488	Remote Similarity	NPD5123	Clinical (unspecified phase)

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