NPASS Compound

Structure

CID291712 OpenBabel06191716102D 28 30 0 0 1 0 0 0 0 0999 V2000 9.6113 3.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.6113 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2872 2.7770 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3578 -0.6045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1472 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2812 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8793 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5491 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7453 1.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 7.0132 1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 2.5691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.6180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -0.1910 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 -1.1910 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5878 0.8090 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 0.3090 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 6 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 6 13 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 17 1 0 0 0 0 9 13 1 0 0 0 0 9 14 2 0 0 0 0 10 16 1 0 0 0 0 10 17 2 0 0 0 0 11 16 2 0 0 0 0 11 19 1 0 0 0 0 12 18 2 0 0 0 0 12 27 1 0 0 0 0 13 2 1 6 0 0 0 15 20 1 0 0 0 0 15 24 2 0 0 0 0 16 18 1 0 0 0 0 17 27 1 0 0 0 0 18 21 1 0 0 0 0 19 20 2 0 0 0 0 19 23 1 0 0 0 0 20 22 1 0 0 0 0 21 23 1 0 0 0 0 21 25 2 0 0 0 0 22 26 2 0 0 0 0 22 28 1 0 0 0 0 23 5 1 1 0 0 0 23 28 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	380.16
Volume:	400.918
LogP:	3.836
LogD:	2.489
LogS:	-4.643
# Rotatable Bonds:	5
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.409
Synthetic Accessibility Score:	4.638
Fsp3:	0.348
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
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:	-4.866
MDCK Permeability:	1.8525779523770325e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.031
Human Intestinal Absorption (HIA):	0.628
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.93

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008
Plasma Protein Binding (PPB):	87.97146606445312%
Volume Distribution (VD):	1.746
Pgp-substrate:	7.990743160247803%

ADMET: Metabolism

CYP1A2-inhibitor:	0.892
CYP1A2-substrate:	0.789
CYP2C19-inhibitor:	0.921
CYP2C19-substrate:	0.385
CYP2C9-inhibitor:	0.922
CYP2C9-substrate:	0.108
CYP2D6-inhibitor:	0.73
CYP2D6-substrate:	0.077
CYP3A4-inhibitor:	0.929
CYP3A4-substrate:	0.544

ADMET: Excretion

Clearance (CL):	1.383
Half-life (T1/2):	0.777

ADMET: Toxicity

hERG Blockers:	0.01
Human Hepatotoxicity (H-HT):	0.974
Drug-inuced Liver Injury (DILI):	0.973
AMES Toxicity:	0.984
Rat Oral Acute Toxicity:	0.976
Maximum Recommended Daily Dose:	0.963
Skin Sensitization:	0.959
Carcinogencity:	0.957
Eye Corrosion:	0.003
Eye Irritation:	0.105
Respiratory Toxicity:	0.86

Download Data

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

Natural Product: NPC291712

Natural Product ID:	NPC291712
*Common Name:**	(-)-Rotiorin
IUPAC Name:	(9aR)-3-acetyl-6-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dienyl]-9a-methylfuro[3,2-g]isochromene-2,9-dione
Synonyms:	(-)-Rotiorin
Standard InCHIKey:	CJMOMVNHRUTOJX-SEAFAFSMSA-N
Standard InCHI:	InChI=1S/C23H24O5/c1-6-13(2)9-14(3)7-8-17-10-16-11-19-20(15(4)24)22(26)28-23(19,5)21(25)18(16)12-27-17/h7-13H,6H2,1-5H3/b8-7+,14-9+/t13-,23+/m0/s1
SMILES:	CC[C@H](C)/C=C(C)/C=C/C1=CC2=CC3=C(C(=O)C)C(=O)O[C@@]3(C)C(=O)C2=CO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL498258
PubChem CID:	11574449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0001831] Carbonyl compounds [CHEMONTID:0000118] Ketones [CHEMONTID:0003487] Cyclic ketones [CHEMONTID:0004325] Cyclohexenones

*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
NPO31359	Chaetomium cupreum	Species	Chaetomiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16792406]

☑ 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	1

Activity Type	# Activity
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20	Organism	Candida albicans	Candida albicans	IC50	=	24.3	ug.mL-1	PMID[486847]

☑ 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 NPC291712 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	200
0.1-0.2	1402
0.2-0.3	6608
0.3-0.4	15869
0.4-0.5	12625
0.5-0.6	4764
0.6-0.7	1092
0.7-0.8	118
0.8-0.85	6
0.85-0.9	8
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.939	High Similarity	NPC281172
0.9186	High Similarity	NPC32944
0.9186	High Similarity	NPC193396
0.9091	High Similarity	NPC12727
0.8977	High Similarity	NPC143210
0.8966	High Similarity	NPC166110
0.8953	High Similarity	NPC95364
0.8953	High Similarity	NPC142159
0.8864	High Similarity	NPC248193
0.875	High Similarity	NPC32552
0.8636	High Similarity	NPC224270
0.8444	Intermediate Similarity	NPC29798
0.8444	Intermediate Similarity	NPC282644
0.8404	Intermediate Similarity	NPC469851
0.8061	Intermediate Similarity	NPC469852
0.8041	Intermediate Similarity	NPC25666
0.8041	Intermediate Similarity	NPC271059
0.8	Intermediate Similarity	NPC470693
0.798	Intermediate Similarity	NPC199107
0.798	Intermediate Similarity	NPC232969
0.7979	Intermediate Similarity	NPC318082
0.7976	Intermediate Similarity	NPC471225
0.7872	Intermediate Similarity	NPC471698
0.78	Intermediate Similarity	NPC469853
0.7711	Intermediate Similarity	NPC287878
0.7692	Intermediate Similarity	NPC321496
0.7684	Intermediate Similarity	NPC31021
0.7667	Intermediate Similarity	NPC130030
0.764	Intermediate Similarity	NPC288281
0.7625	Intermediate Similarity	NPC191233
0.76	Intermediate Similarity	NPC272528
0.7558	Intermediate Similarity	NPC473825
0.75	Intermediate Similarity	NPC470688
0.75	Intermediate Similarity	NPC220766
0.7444	Intermediate Similarity	NPC16488
0.7412	Intermediate Similarity	NPC470686
0.7379	Intermediate Similarity	NPC327106
0.732	Intermediate Similarity	NPC295347
0.7312	Intermediate Similarity	NPC125925
0.73	Intermediate Similarity	NPC471699
0.7283	Intermediate Similarity	NPC67081
0.7283	Intermediate Similarity	NPC471223
0.7273	Intermediate Similarity	NPC99182
0.7253	Intermediate Similarity	NPC118423
0.7253	Intermediate Similarity	NPC475083
0.7234	Intermediate Similarity	NPC475902
0.7204	Intermediate Similarity	NPC316426
0.7204	Intermediate Similarity	NPC168248
0.7204	Intermediate Similarity	NPC315395
0.7172	Intermediate Similarity	NPC208094
0.7158	Intermediate Similarity	NPC280833
0.7143	Intermediate Similarity	NPC232812
0.7143	Intermediate Similarity	NPC268122
0.7129	Intermediate Similarity	NPC224172
0.7128	Intermediate Similarity	NPC103743
0.7128	Intermediate Similarity	NPC476079
0.7128	Intermediate Similarity	NPC113370
0.7108	Intermediate Similarity	NPC203335
0.7097	Intermediate Similarity	NPC307112
0.7093	Intermediate Similarity	NPC12815
0.7093	Intermediate Similarity	NPC238948
0.7093	Intermediate Similarity	NPC215745
0.7079	Intermediate Similarity	NPC469510
0.7073	Intermediate Similarity	NPC182794
0.7071	Intermediate Similarity	NPC299396
0.7071	Intermediate Similarity	NPC301596
0.7071	Intermediate Similarity	NPC172998
0.7059	Intermediate Similarity	NPC37929
0.7059	Intermediate Similarity	NPC64234
0.7053	Intermediate Similarity	NPC471047
0.7053	Intermediate Similarity	NPC469628
0.7053	Intermediate Similarity	NPC260343
0.7053	Intermediate Similarity	NPC475906
0.7053	Intermediate Similarity	NPC469631
0.7053	Intermediate Similarity	NPC469653
0.7033	Intermediate Similarity	NPC42470
0.7024	Intermediate Similarity	NPC470256
0.7024	Intermediate Similarity	NPC477117
0.7021	Intermediate Similarity	NPC472863
0.7021	Intermediate Similarity	NPC261721
0.7021	Intermediate Similarity	NPC279859
0.7021	Intermediate Similarity	NPC38576
0.7011	Intermediate Similarity	NPC15499
0.7011	Intermediate Similarity	NPC259599
0.7011	Intermediate Similarity	NPC294434
0.7011	Intermediate Similarity	NPC117746
0.7011	Intermediate Similarity	NPC122244
0.7011	Intermediate Similarity	NPC474758
0.7	Intermediate Similarity	NPC271632
0.7	Intermediate Similarity	NPC473981
0.7	Intermediate Similarity	NPC134083
0.7	Intermediate Similarity	NPC243298
0.7	Intermediate Similarity	NPC473980
0.6979	Remote Similarity	NPC64913
0.6979	Remote Similarity	NPC242877
0.6977	Remote Similarity	NPC133098
0.697	Remote Similarity	NPC209355
0.697	Remote Similarity	NPC234339
0.697	Remote Similarity	NPC273197
0.6966	Remote Similarity	NPC68156
0.6966	Remote Similarity	NPC180290
0.6957	Remote Similarity	NPC475690
0.6957	Remote Similarity	NPC10080
0.6957	Remote Similarity	NPC94200
0.6957	Remote Similarity	NPC471326
0.6957	Remote Similarity	NPC123908
0.6957	Remote Similarity	NPC221231
0.6941	Remote Similarity	NPC473277
0.6941	Remote Similarity	NPC151481
0.6941	Remote Similarity	NPC265574
0.6939	Remote Similarity	NPC1108
0.6923	Remote Similarity	NPC268827
0.6915	Remote Similarity	NPC189311
0.6907	Remote Similarity	NPC280592
0.6907	Remote Similarity	NPC469372
0.6907	Remote Similarity	NPC253177
0.6907	Remote Similarity	NPC213636
0.6907	Remote Similarity	NPC475879
0.6905	Remote Similarity	NPC21998
0.6905	Remote Similarity	NPC194871
0.6889	Remote Similarity	NPC475699
0.6889	Remote Similarity	NPC264391
0.6881	Remote Similarity	NPC326264
0.6875	Remote Similarity	NPC471956
0.6875	Remote Similarity	NPC241507
0.6875	Remote Similarity	NPC26078
0.6875	Remote Similarity	NPC245320
0.6875	Remote Similarity	NPC196407
0.6875	Remote Similarity	NPC473658
0.6875	Remote Similarity	NPC472302
0.6875	Remote Similarity	NPC133600
0.6869	Remote Similarity	NPC471994
0.6869	Remote Similarity	NPC166143
0.6869	Remote Similarity	NPC476596
0.6869	Remote Similarity	NPC38830
0.6869	Remote Similarity	NPC120351
0.6863	Remote Similarity	NPC215253
0.6863	Remote Similarity	NPC54705
0.6863	Remote Similarity	NPC185253
0.686	Remote Similarity	NPC315285
0.686	Remote Similarity	NPC59558
0.6854	Remote Similarity	NPC123360
0.6854	Remote Similarity	NPC51391
0.6854	Remote Similarity	NPC27205
0.6854	Remote Similarity	NPC4509
0.6854	Remote Similarity	NPC4492
0.6848	Remote Similarity	NPC275507
0.6842	Remote Similarity	NPC234038
0.6837	Remote Similarity	NPC471329
0.6837	Remote Similarity	NPC45579
0.6837	Remote Similarity	NPC32494
0.6837	Remote Similarity	NPC175842
0.6837	Remote Similarity	NPC296114
0.6829	Remote Similarity	NPC210303
0.6829	Remote Similarity	NPC44343
0.6829	Remote Similarity	NPC179087
0.6827	Remote Similarity	NPC297281
0.6827	Remote Similarity	NPC473144
0.6822	Remote Similarity	NPC23497
0.6822	Remote Similarity	NPC137911
0.6822	Remote Similarity	NPC228477
0.6818	Remote Similarity	NPC476355
0.6814	Remote Similarity	NPC476815
0.6814	Remote Similarity	NPC31641
0.6814	Remote Similarity	NPC473145
0.6813	Remote Similarity	NPC471299
0.6813	Remote Similarity	NPC178277
0.6809	Remote Similarity	NPC469884
0.6809	Remote Similarity	NPC30486
0.6804	Remote Similarity	NPC51358
0.6804	Remote Similarity	NPC474844
0.6804	Remote Similarity	NPC284561
0.6804	Remote Similarity	NPC307092
0.6796	Remote Similarity	NPC168319
0.6796	Remote Similarity	NPC194028
0.6792	Remote Similarity	NPC266514
0.679	Remote Similarity	NPC79756
0.679	Remote Similarity	NPC309408
0.6789	Remote Similarity	NPC66108
0.6786	Remote Similarity	NPC248125
0.6782	Remote Similarity	NPC181587
0.6782	Remote Similarity	NPC257618
0.6782	Remote Similarity	NPC474539
0.6778	Remote Similarity	NPC315394
0.6778	Remote Similarity	NPC54996
0.6778	Remote Similarity	NPC316324
0.6778	Remote Similarity	NPC57744
0.6774	Remote Similarity	NPC471218
0.6774	Remote Similarity	NPC26624
0.6774	Remote Similarity	NPC85772
0.6771	Remote Similarity	NPC75315
0.6771	Remote Similarity	NPC266957
0.6771	Remote Similarity	NPC163016
0.6771	Remote Similarity	NPC478145
0.6768	Remote Similarity	NPC469939
0.6768	Remote Similarity	NPC59646
0.6768	Remote Similarity	NPC476598
0.6768	Remote Similarity	NPC476597
0.6768	Remote Similarity	NPC165383
0.6765	Remote Similarity	NPC264378

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 NPC291712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	182
0.1-0.2	1588
0.2-0.3	4191
0.3-0.4	2332
0.4-0.5	691
0.5-0.6	152
0.6-0.7	14
0.7-0.8	0
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
0.7143	Intermediate Similarity	NPD5209	Approved
0.6778	Remote Similarity	NPD4756	Discovery
0.6421	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD1694	Approved
0.6337	Remote Similarity	NPD5693	Phase 1
0.6337	Remote Similarity	NPD5694	Approved
0.6289	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6279	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6238	Remote Similarity	NPD5692	Phase 3
0.622	Remote Similarity	NPD8779	Phase 3
0.6207	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5737	Approved
0.62	Remote Similarity	NPD6672	Approved
0.6196	Remote Similarity	NPD8039	Approved
0.6176	Remote Similarity	NPD6050	Approved
0.6163	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6132	Remote Similarity	NPD4225	Approved
0.6121	Remote Similarity	NPD7115	Discovery
0.6078	Remote Similarity	NPD5785	Approved
0.6042	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD7637	Suspended
0.6018	Remote Similarity	NPD2067	Discontinued
0.6	Remote Similarity	NPD5695	Phase 3
0.598	Remote Similarity	NPD6904	Approved
0.598	Remote Similarity	NPD6080	Approved
0.598	Remote Similarity	NPD6673	Approved
0.5962	Remote Similarity	NPD5779	Approved
0.5962	Remote Similarity	NPD5778	Approved
0.5922	Remote Similarity	NPD7838	Discovery
0.5905	Remote Similarity	NPD5282	Discontinued
0.59	Remote Similarity	NPD1696	Phase 3
0.59	Remote Similarity	NPD5363	Approved
0.5893	Remote Similarity	NPD5697	Approved
0.5888	Remote Similarity	NPD6084	Phase 2
0.5888	Remote Similarity	NPD6083	Phase 2
0.5859	Remote Similarity	NPD6110	Phase 1
0.5859	Remote Similarity	NPD7154	Phase 3
0.5849	Remote Similarity	NPD5654	Approved
0.5849	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.5841	Remote Similarity	NPD6881	Approved
0.5841	Remote Similarity	NPD6899	Approved
0.5841	Remote Similarity	NPD6011	Approved
0.5833	Remote Similarity	NPD5696	Approved
0.5825	Remote Similarity	NPD6101	Approved
0.5825	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5789	Remote Similarity	NPD6013	Approved
0.5789	Remote Similarity	NPD6014	Approved
0.5789	Remote Similarity	NPD6012	Approved
0.5784	Remote Similarity	NPD3573	Approved
0.5784	Remote Similarity	NPD1282	Approved
0.578	Remote Similarity	NPD6648	Approved
0.5776	Remote Similarity	NPD6053	Discontinued
0.5769	Remote Similarity	NPD5207	Approved
0.5752	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.5741	Remote Similarity	NPD5959	Approved
0.5739	Remote Similarity	NPD6883	Approved
0.5739	Remote Similarity	NPD7290	Approved
0.5739	Remote Similarity	NPD7102	Approved
0.5714	Remote Similarity	NPD6411	Approved
0.5714	Remote Similarity	NPD4252	Approved
0.569	Remote Similarity	NPD6650	Approved
0.569	Remote Similarity	NPD8130	Phase 1
0.569	Remote Similarity	NPD7601	Clinical (unspecified phase)
0.569	Remote Similarity	NPD6869	Approved
0.569	Remote Similarity	NPD6847	Approved
0.569	Remote Similarity	NPD6617	Approved
0.569	Remote Similarity	NPD6649	Approved
0.5688	Remote Similarity	NPD7638	Approved
0.5686	Remote Similarity	NPD5330	Approved
0.5686	Remote Similarity	NPD6098	Approved
0.5686	Remote Similarity	NPD6684	Approved
0.5686	Remote Similarity	NPD7146	Approved
0.5686	Remote Similarity	NPD7521	Approved
0.5686	Remote Similarity	NPD6409	Approved
0.5686	Remote Similarity	NPD7334	Approved
0.5679	Remote Similarity	NPD6927	Phase 3
0.5673	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5673	Remote Similarity	NPD6051	Approved
0.5667	Remote Similarity	NPD3704	Approved
0.5664	Remote Similarity	NPD6402	Approved
0.5664	Remote Similarity	NPD6675	Approved
0.5664	Remote Similarity	NPD5739	Approved
0.5664	Remote Similarity	NPD7128	Approved
0.5657	Remote Similarity	NPD5369	Approved
0.5656	Remote Similarity	NPD8513	Phase 3
0.5641	Remote Similarity	NPD6882	Approved
0.5641	Remote Similarity	NPD8297	Approved
0.5636	Remote Similarity	NPD7639	Approved
0.5636	Remote Similarity	NPD7640	Approved
0.563	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5619	Remote Similarity	NPD6698	Approved
0.5619	Remote Similarity	NPD46	Approved
0.5614	Remote Similarity	NPD5701	Approved
0.56	Remote Similarity	NPD4270	Approved
0.56	Remote Similarity	NPD4269	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