NPASS Compound

Structure

NPC248193 OpenBabel07101719152D 31 33 0 0 1 0 0 0 0 0999 V2000 -6.0757 9.1071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3383 3.1043 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4152 3.3090 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 -5.0976 8.8992 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7885 7.9481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8104 7.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5014 6.7891 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5232 6.5812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2142 5.6302 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2361 5.4223 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9271 4.4712 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0511 4.2633 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 2.6831 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8171 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3601 3.3122 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.5491 2.8090 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 1.8171 1.8090 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 -0.0000 1.6180 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 -0.3090 2.5691 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 2 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 -1.2872 2.7770 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 2.6831 3.3090 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 5 1 0 0 0 0 3 18 1 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 8 1 0 0 0 0 8 9 1 0 0 0 0 9 10 1 0 0 0 0 10 11 1 0 0 0 0 11 12 1 0 0 0 0 12 13 1 0 0 0 0 13 17 1 0 0 0 0 14 18 2 0 0 0 0 14 19 1 0 0 0 0 15 19 2 0 0 0 0 15 21 1 0 0 0 0 16 20 2 0 0 0 0 16 30 1 0 0 0 0 17 2 1 6 0 0 0 17 24 1 0 0 0 0 18 30 1 0 0 0 0 19 20 1 0 0 0 0 20 23 1 0 0 0 0 21 26 1 0 0 0 0 21 27 2 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 23 26 1 0 0 0 0 24 28 2 0 0 0 0 25 29 2 0 0 0 0 25 31 1 0 0 0 0 26 4 1 1 0 0 0 26 31 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	426.24
Volume:	458.079
LogP:	6.213
LogD:	3.442
LogS:	-6.201
# Rotatable Bonds:	11
TPSA:	69.67
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.242
Synthetic Accessibility Score:	4.193
Fsp3:	0.577
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.015
MDCK Permeability:	1.861320561147295e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.011
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	1.0
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043
Plasma Protein Binding (PPB):	97.30746459960938%
Volume Distribution (VD):	3.037
Pgp-substrate:	3.085453987121582%

ADMET: Metabolism

CYP1A2-inhibitor:	0.456
CYP1A2-substrate:	0.608
CYP2C19-inhibitor:	0.863
CYP2C19-substrate:	0.382
CYP2C9-inhibitor:	0.851
CYP2C9-substrate:	0.06
CYP2D6-inhibitor:	0.814
CYP2D6-substrate:	0.019
CYP3A4-inhibitor:	0.914
CYP3A4-substrate:	0.375

ADMET: Excretion

Clearance (CL):	1.867
Half-life (T1/2):	0.183

ADMET: Toxicity

hERG Blockers:	0.256
Human Hepatotoxicity (H-HT):	0.907
Drug-inuced Liver Injury (DILI):	0.94
AMES Toxicity:	0.937
Rat Oral Acute Toxicity:	0.818
Maximum Recommended Daily Dose:	0.815
Skin Sensitization:	0.955
Carcinogencity:	0.873
Eye Corrosion:	0.003
Eye Irritation:	0.02
Respiratory Toxicity:	0.783

Download Data

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

Natural Product: NPC248193

Natural Product ID:	NPC248193
*Common Name:**	(6Ar)-3,6A-Dimethyl-9-[(2S)-2-Methyldodecanoyl]Furo[2,3-H]Isochromene-6,8-Dione
IUPAC Name:	(6aR)-3,6a-dimethyl-9-[(2S)-2-methyldodecanoyl]furo[2,3-h]isochromene-6,8-dione
Synonyms:
Standard InCHIKey:	VWGYSDWIZCHBOH-QLXKLKPCSA-N
Standard InCHI:	InChI=1S/C26H34O5/c1-5-6-7-8-9-10-11-12-13-17(2)24(28)22-23-20-16-30-18(3)14-19(20)15-21(27)26(23,4)31-25(22)29/h14-17H,5-13H2,1-4H3/t17-,26-/m0/s1
SMILES:	CCCCCCCCCC[C@H](C)C(=O)C1=C2C3=COC(=CC3=CC(=O)[C@]2(C)OC1=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1215536
PubChem CID:	49864151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002518] Annonaceous acetogenins

*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
NPO33002	aspergillus deflectus cbs 109.55	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20655237]

☑ 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	4

Activity Type	# Activity
Cell Line	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT397	Cell Line	NCI-H460	Homo sapiens	IC50	>	50000.0	nM	PMID[571180]
NPT762	Cell Line	A-431	Homo sapiens	IC50	>	25000.0	nM	PMID[571180]
NPT2	Others	Unspecified		IC50	>	50000.0	nM	PMID[571180]
NPT2	Others	Unspecified		IC50	>	100000.0	nM	PMID[571180]

☑ 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 NPC248193 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	1293
0.2-0.3	5111
0.3-0.4	11197
0.4-0.5	15256
0.5-0.6	6901
0.6-0.7	2336
0.7-0.8	346
0.8-0.85	17
0.85-0.9	8
0.9-0.95	1
0.95-1	7

Similarity Score	Similarity Level	Natural Product ID
0.9884	High Similarity	NPC166110
0.9651	High Similarity	NPC95364
0.9651	High Similarity	NPC142159
0.9432	High Similarity	NPC193396
0.9432	High Similarity	NPC32944
0.8966	High Similarity	NPC281172
0.8864	High Similarity	NPC291712
0.866	High Similarity	NPC271059
0.866	High Similarity	NPC25666
0.8646	High Similarity	NPC469851
0.8602	High Similarity	NPC143210
0.8511	High Similarity	NPC12727
0.8511	High Similarity	NPC31021
0.83	Intermediate Similarity	NPC469852
0.8265	Intermediate Similarity	NPC471699
0.8218	Intermediate Similarity	NPC469853
0.8191	Intermediate Similarity	NPC32552
0.8125	Intermediate Similarity	NPC471698
0.8095	Intermediate Similarity	NPC321496
0.8085	Intermediate Similarity	NPC224270
0.8046	Intermediate Similarity	NPC471225
0.7979	Intermediate Similarity	NPC280833
0.7938	Intermediate Similarity	NPC295347
0.7864	Intermediate Similarity	NPC199107
0.7864	Intermediate Similarity	NPC232969
0.7857	Intermediate Similarity	NPC318082
0.7778	Intermediate Similarity	NPC208094
0.7766	Intermediate Similarity	NPC103743
0.7766	Intermediate Similarity	NPC476079
0.7766	Intermediate Similarity	NPC113370
0.7732	Intermediate Similarity	NPC282644
0.7732	Intermediate Similarity	NPC29798
0.7732	Intermediate Similarity	NPC476598
0.7732	Intermediate Similarity	NPC476597
0.7708	Intermediate Similarity	NPC253177
0.7708	Intermediate Similarity	NPC280592
0.7708	Intermediate Similarity	NPC213636
0.7684	Intermediate Similarity	NPC469631
0.7684	Intermediate Similarity	NPC469628
0.7684	Intermediate Similarity	NPC471047
0.7684	Intermediate Similarity	NPC469653
0.7684	Intermediate Similarity	NPC473658
0.7684	Intermediate Similarity	NPC475902
0.7684	Intermediate Similarity	NPC475906
0.7684	Intermediate Similarity	NPC472302
0.7677	Intermediate Similarity	NPC172998
0.7677	Intermediate Similarity	NPC299396
0.7677	Intermediate Similarity	NPC301596
0.766	Intermediate Similarity	NPC279859
0.766	Intermediate Similarity	NPC261721
0.766	Intermediate Similarity	NPC38576
0.7653	Intermediate Similarity	NPC476596
0.764	Intermediate Similarity	NPC316324
0.764	Intermediate Similarity	NPC180290
0.7629	Intermediate Similarity	NPC296114
0.7629	Intermediate Similarity	NPC471329
0.7624	Intermediate Similarity	NPC54705
0.7609	Intermediate Similarity	NPC471326
0.7609	Intermediate Similarity	NPC221231
0.7604	Intermediate Similarity	NPC284561
0.7604	Intermediate Similarity	NPC307092
0.76	Intermediate Similarity	NPC239895
0.7579	Intermediate Similarity	NPC471739
0.7576	Intermediate Similarity	NPC234339
0.7576	Intermediate Similarity	NPC273197
0.7558	Intermediate Similarity	NPC64234
0.7558	Intermediate Similarity	NPC37929
0.7556	Intermediate Similarity	NPC471220
0.7556	Intermediate Similarity	NPC315765
0.7553	Intermediate Similarity	NPC307112
0.7553	Intermediate Similarity	NPC189311
0.7551	Intermediate Similarity	NPC1108
0.7547	Intermediate Similarity	NPC23497
0.7545	Intermediate Similarity	NPC243298
0.7527	Intermediate Similarity	NPC193198
0.7527	Intermediate Similarity	NPC288281
0.7527	Intermediate Similarity	NPC16488
0.7526	Intermediate Similarity	NPC212679
0.7526	Intermediate Similarity	NPC469595
0.7526	Intermediate Similarity	NPC220454
0.7526	Intermediate Similarity	NPC469372
0.7525	Intermediate Similarity	NPC264378
0.75	Intermediate Similarity	NPC272528
0.75	Intermediate Similarity	NPC471325
0.75	Intermediate Similarity	NPC26078
0.75	Intermediate Similarity	NPC241507
0.7475	Intermediate Similarity	NPC38830
0.7475	Intermediate Similarity	NPC477241
0.7474	Intermediate Similarity	NPC203795
0.7474	Intermediate Similarity	NPC220478
0.7474	Intermediate Similarity	NPC315395
0.7474	Intermediate Similarity	NPC472009
0.7474	Intermediate Similarity	NPC316426
0.7473	Intermediate Similarity	NPC150646
0.7473	Intermediate Similarity	NPC471740
0.7473	Intermediate Similarity	NPC471299
0.7449	Intermediate Similarity	NPC45579
0.7447	Intermediate Similarity	NPC470918
0.7447	Intermediate Similarity	NPC30486
0.7447	Intermediate Similarity	NPC474359
0.7442	Intermediate Similarity	NPC232812
0.7426	Intermediate Similarity	NPC53844
0.7423	Intermediate Similarity	NPC51358
0.7419	Intermediate Similarity	NPC268122
0.7416	Intermediate Similarity	NPC469414
0.7416	Intermediate Similarity	NPC329826
0.7411	Intermediate Similarity	NPC245320
0.7404	Intermediate Similarity	NPC297281
0.7404	Intermediate Similarity	NPC473144
0.74	Intermediate Similarity	NPC209355
0.7396	Intermediate Similarity	NPC125925
0.7396	Intermediate Similarity	NPC478145
0.7396	Intermediate Similarity	NPC472007
0.7383	Intermediate Similarity	NPC228477
0.7383	Intermediate Similarity	NPC137911
0.7379	Intermediate Similarity	NPC168319
0.7379	Intermediate Similarity	NPC194028
0.7368	Intermediate Similarity	NPC471223
0.7368	Intermediate Similarity	NPC67081
0.7363	Intermediate Similarity	NPC128276
0.7353	Intermediate Similarity	NPC35717
0.7347	Intermediate Similarity	NPC51653
0.7347	Intermediate Similarity	NPC316228
0.7347	Intermediate Similarity	NPC471818
0.7345	Intermediate Similarity	NPC473145
0.7345	Intermediate Similarity	NPC476815
0.7345	Intermediate Similarity	NPC31641
0.734	Intermediate Similarity	NPC475989
0.734	Intermediate Similarity	NPC118423
0.734	Intermediate Similarity	NPC475947
0.734	Intermediate Similarity	NPC475083
0.734	Intermediate Similarity	NPC222358
0.7333	Intermediate Similarity	NPC27205
0.7321	Intermediate Similarity	NPC315974
0.732	Intermediate Similarity	NPC472008
0.7312	Intermediate Similarity	NPC475481
0.7312	Intermediate Similarity	NPC42470
0.7312	Intermediate Similarity	NPC282293
0.7312	Intermediate Similarity	NPC79277
0.7312	Intermediate Similarity	NPC286229
0.7308	Intermediate Similarity	NPC197835
0.7308	Intermediate Similarity	NPC291500
0.7308	Intermediate Similarity	NPC140591
0.7308	Intermediate Similarity	NPC189609
0.7308	Intermediate Similarity	NPC303653
0.7303	Intermediate Similarity	NPC474551
0.73	Intermediate Similarity	NPC148463
0.73	Intermediate Similarity	NPC470697
0.73	Intermediate Similarity	NPC469632
0.7292	Intermediate Similarity	NPC472863
0.7292	Intermediate Similarity	NPC234038
0.7292	Intermediate Similarity	NPC168248
0.729	Intermediate Similarity	NPC322903
0.729	Intermediate Similarity	NPC327106
0.7283	Intermediate Similarity	NPC178277
0.7282	Intermediate Similarity	NPC474012
0.7282	Intermediate Similarity	NPC469551
0.7282	Intermediate Similarity	NPC476299
0.7273	Intermediate Similarity	NPC478244
0.7273	Intermediate Similarity	NPC20713
0.7273	Intermediate Similarity	NPC478243
0.7273	Intermediate Similarity	NPC326264
0.7273	Intermediate Similarity	NPC472705
0.7255	Intermediate Similarity	NPC110937
0.7255	Intermediate Similarity	NPC2049
0.7255	Intermediate Similarity	NPC134083
0.7253	Intermediate Similarity	NPC57744
0.7253	Intermediate Similarity	NPC283087
0.7253	Intermediate Similarity	NPC187568
0.7253	Intermediate Similarity	NPC41780
0.7248	Intermediate Similarity	NPC324683
0.7245	Intermediate Similarity	NPC5509
0.7238	Intermediate Similarity	NPC473283
0.7238	Intermediate Similarity	NPC475526
0.7238	Intermediate Similarity	NPC329345
0.7234	Intermediate Similarity	NPC173609
0.7234	Intermediate Similarity	NPC35556
0.7234	Intermediate Similarity	NPC471218
0.7234	Intermediate Similarity	NPC10080
0.7234	Intermediate Similarity	NPC85772
0.7234	Intermediate Similarity	NPC123908
0.7234	Intermediate Similarity	NPC475690
0.7228	Intermediate Similarity	NPC127197
0.7228	Intermediate Similarity	NPC474490
0.7228	Intermediate Similarity	NPC470978
0.7228	Intermediate Similarity	NPC470974
0.7222	Intermediate Similarity	NPC38154
0.7216	Intermediate Similarity	NPC471738
0.7216	Intermediate Similarity	NPC181327
0.7216	Intermediate Similarity	NPC478144
0.7212	Intermediate Similarity	NPC469657
0.7212	Intermediate Similarity	NPC244456
0.7212	Intermediate Similarity	NPC472643
0.72	Intermediate Similarity	NPC271652
0.7191	Intermediate Similarity	NPC238425
0.7191	Intermediate Similarity	NPC472018
0.7191	Intermediate Similarity	NPC474543
0.7191	Intermediate Similarity	NPC287878
0.7188	Intermediate Similarity	NPC130030
0.7188	Intermediate Similarity	NPC470177

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 NPC248193 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	206
0.1-0.2	1587
0.2-0.3	3656
0.3-0.4	2478
0.4-0.5	886
0.5-0.6	274
0.6-0.7	61
0.7-0.8	2
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
0.7253	Intermediate Similarity	NPD4756	Discovery
0.7143	Intermediate Similarity	NPD5737	Approved
0.7143	Intermediate Similarity	NPD6672	Approved
0.71	Intermediate Similarity	NPD5693	Phase 1
0.71	Intermediate Similarity	NPD6050	Approved
0.7053	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD8039	Approved
0.7	Intermediate Similarity	NPD5692	Phase 3
0.6931	Remote Similarity	NPD5694	Approved
0.69	Remote Similarity	NPD6080	Approved
0.69	Remote Similarity	NPD6673	Approved
0.69	Remote Similarity	NPD6904	Approved
0.6875	Remote Similarity	NPD5209	Approved
0.6837	Remote Similarity	NPD1694	Approved
0.6762	Remote Similarity	NPD6084	Phase 2
0.6762	Remote Similarity	NPD6083	Phase 2
0.6731	Remote Similarity	NPD5695	Phase 3
0.6705	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD5779	Approved
0.6699	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5785	Approved
0.6638	Remote Similarity	NPD7115	Discovery
0.6633	Remote Similarity	NPD7154	Phase 3
0.66	Remote Similarity	NPD7146	Approved
0.66	Remote Similarity	NPD6409	Approved
0.66	Remote Similarity	NPD7334	Approved
0.66	Remote Similarity	NPD7521	Approved
0.66	Remote Similarity	NPD6098	Approved
0.66	Remote Similarity	NPD5330	Approved
0.66	Remote Similarity	NPD6684	Approved
0.6579	Remote Similarity	NPD6053	Discontinued
0.6571	Remote Similarity	NPD5654	Approved
0.6569	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD6101	Approved
0.6569	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6549	Remote Similarity	NPD2067	Discontinued
0.6542	Remote Similarity	NPD5696	Approved
0.6505	Remote Similarity	NPD46	Approved
0.6505	Remote Similarity	NPD6698	Approved
0.65	Remote Similarity	NPD5363	Approved
0.6486	Remote Similarity	NPD6402	Approved
0.6486	Remote Similarity	NPD7128	Approved
0.6486	Remote Similarity	NPD5739	Approved
0.6486	Remote Similarity	NPD6675	Approved
0.6476	Remote Similarity	NPD5282	Discontinued
0.6471	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD6903	Approved
0.6449	Remote Similarity	NPD5959	Approved
0.6442	Remote Similarity	NPD6411	Approved
0.6429	Remote Similarity	NPD5369	Approved
0.6429	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6404	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD6399	Phase 3
0.6372	Remote Similarity	NPD6899	Approved
0.6372	Remote Similarity	NPD7320	Approved
0.6372	Remote Similarity	NPD6881	Approved
0.6364	Remote Similarity	NPD4270	Approved
0.6364	Remote Similarity	NPD4269	Approved
0.6346	Remote Similarity	NPD5207	Approved
0.6333	Remote Similarity	NPD3704	Approved
0.6327	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD7748	Approved
0.6321	Remote Similarity	NPD7900	Approved
0.6316	Remote Similarity	NPD6373	Approved
0.6316	Remote Similarity	NPD6372	Approved
0.6286	Remote Similarity	NPD7983	Approved
0.6283	Remote Similarity	NPD5697	Approved
0.6283	Remote Similarity	NPD5701	Approved
0.6281	Remote Similarity	NPD8513	Phase 3
0.6275	Remote Similarity	NPD5786	Approved
0.6262	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6262	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6261	Remote Similarity	NPD7290	Approved
0.6261	Remote Similarity	NPD7102	Approved
0.6261	Remote Similarity	NPD6883	Approved
0.6239	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD7638	Approved
0.6239	Remote Similarity	NPD4225	Approved
0.6228	Remote Similarity	NPD6011	Approved
0.6214	Remote Similarity	NPD3573	Approved
0.6207	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6847	Approved
0.6207	Remote Similarity	NPD6650	Approved
0.6207	Remote Similarity	NPD6649	Approved
0.6207	Remote Similarity	NPD6869	Approved
0.6207	Remote Similarity	NPD8130	Phase 1
0.6207	Remote Similarity	NPD6617	Approved
0.6204	Remote Similarity	NPD7839	Suspended
0.62	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7639	Approved
0.6182	Remote Similarity	NPD7640	Approved
0.6176	Remote Similarity	NPD1696	Phase 3
0.6176	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6012	Approved
0.6174	Remote Similarity	NPD6013	Approved
0.6174	Remote Similarity	NPD6014	Approved
0.6162	Remote Similarity	NPD4695	Discontinued
0.6162	Remote Similarity	NPD4252	Approved
0.6154	Remote Similarity	NPD8297	Approved
0.6154	Remote Similarity	NPD7331	Phase 2
0.6154	Remote Similarity	NPD6882	Approved
0.6154	Remote Similarity	NPD5208	Approved
0.6148	Remote Similarity	NPD8517	Approved
0.6148	Remote Similarity	NPD8515	Approved
0.6148	Remote Similarity	NPD8516	Approved
0.6147	Remote Similarity	NPD7902	Approved
0.6139	Remote Similarity	NPD5362	Discontinued
0.6132	Remote Similarity	NPD7515	Phase 2
0.6132	Remote Similarity	NPD5281	Approved
0.6132	Remote Similarity	NPD7637	Suspended
0.6132	Remote Similarity	NPD5284	Approved
0.6121	Remote Similarity	NPD6371	Approved
0.6117	Remote Similarity	NPD5280	Approved
0.6117	Remote Similarity	NPD5279	Phase 3
0.6117	Remote Similarity	NPD4694	Approved
0.6111	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4753	Phase 2
0.6095	Remote Similarity	NPD6051	Approved
0.6068	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6008	Approved
0.6038	Remote Similarity	NPD7838	Discovery
0.6019	Remote Similarity	NPD5329	Approved
0.6	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6	Remote Similarity	NPD690	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6614	Approved
0.598	Remote Similarity	NPD6110	Phase 1
0.5977	Remote Similarity	NPD8779	Phase 3
0.5969	Remote Similarity	NPD7260	Phase 2
0.5965	Remote Similarity	NPD5909	Discontinued
0.596	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6686	Approved
0.5943	Remote Similarity	NPD1695	Approved
0.5935	Remote Similarity	NPD6319	Approved
0.5935	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4786	Approved
0.5922	Remote Similarity	NPD4197	Approved
0.5922	Remote Similarity	NPD3668	Phase 3
0.5906	Remote Similarity	NPD8074	Phase 3
0.5902	Remote Similarity	NPD6335	Approved
0.5897	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.5893	Remote Similarity	NPD6648	Approved
0.5882	Remote Similarity	NPD3667	Approved
0.5882	Remote Similarity	NPD6435	Approved
0.5876	Remote Similarity	NPD5733	Approved
0.5873	Remote Similarity	NPD7492	Approved
0.5872	Remote Similarity	NPD6001	Approved
0.587	Remote Similarity	NPD7341	Phase 2
0.5868	Remote Similarity	NPD6868	Approved
0.5868	Remote Similarity	NPD6274	Approved
0.5865	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5856	Remote Similarity	NPD4755	Approved
0.5854	Remote Similarity	NPD7100	Approved
0.5854	Remote Similarity	NPD7101	Approved
0.5847	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4820	Approved
0.5842	Remote Similarity	NPD4819	Approved
0.5842	Remote Similarity	NPD4821	Approved
0.5842	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5842	Remote Similarity	NPD4822	Approved
0.5833	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6616	Approved
0.582	Remote Similarity	NPD6317	Approved
0.5818	Remote Similarity	NPD5210	Approved
0.5818	Remote Similarity	NPD4629	Approved
0.581	Remote Similarity	NPD6422	Discontinued
0.581	Remote Similarity	NPD5690	Phase 2
0.581	Remote Similarity	NPD4519	Discontinued
0.581	Remote Similarity	NPD4623	Approved
0.581	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.581	Remote Similarity	NPD3618	Phase 1
0.5806	Remote Similarity	NPD6059	Approved
0.5806	Remote Similarity	NPD6054	Approved
0.58	Remote Similarity	NPD3617	Approved
0.5794	Remote Similarity	NPD5328	Approved
0.5794	Remote Similarity	NPD5370	Suspended
0.5789	Remote Similarity	NPD5211	Phase 2
0.5781	Remote Similarity	NPD7078	Approved
0.5781	Remote Similarity	NPD8293	Discontinued
0.5772	Remote Similarity	NPD6313	Approved
0.5772	Remote Similarity	NPD6314	Approved
0.5769	Remote Similarity	NPD3665	Phase 1
0.5769	Remote Similarity	NPD3666	Approved
0.5769	Remote Similarity	NPD3133	Approved
0.5766	Remote Similarity	NPD4697	Phase 3
0.5766	Remote Similarity	NPD5221	Approved
0.5766	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5766	Remote Similarity	NPD5222	Approved
0.576	Remote Similarity	NPD6908	Approved
0.576	Remote Similarity	NPD6909	Approved
0.5755	Remote Similarity	NPD4250	Approved
0.5755	Remote Similarity	NPD4251	Approved
0.5752	Remote Similarity	NPD4700	Approved
0.5752	Remote Similarity	NPD5286	Approved
0.5752	Remote Similarity	NPD4696	Approved
0.5752	Remote Similarity	NPD5285	Approved
0.5739	Remote Similarity	NPD6052	Approved
0.5736	Remote Similarity	NPD7736	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