NPASS Compound

Structure

NPC474899 OpenBabel07101719512D 25 28 0 0 1 0 0 0 0 0999 V2000 -3.4051 1.4483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 -1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6015 1.9914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7328 3.7792 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6980 0.7412 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 -1.7321 0.0000 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 2.2174 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 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.3587 2.7247 0.0000 C 0 0 0 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 0 0 0 0 0 0 0 0 0 0 -0.8660 2.2174 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 -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 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7899 2.6001 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7414 3.6486 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3587 2.7247 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 2 0 0 0 0 2 18 1 0 0 0 0 3 18 1 0 0 0 0 5 23 1 0 0 0 0 6 19 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 19 1 0 0 0 0 9 11 2 0 0 0 0 9 12 1 0 0 0 0 10 11 1 0 0 0 0 10 14 2 0 0 0 0 11 20 1 0 0 0 0 12 16 1 1 0 0 0 12 18 1 0 0 0 0 13 18 1 0 0 0 0 13 20 1 6 0 0 0 14 23 1 0 0 0 0 14 24 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 6 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 16 25 1 0 0 0 0 17 22 2 0 0 0 0 17 24 1 0 0 0 0 19 4 1 6 0 0 0 20 25 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	344.16
Volume:	351.019
LogP:	3.017
LogD:	2.731
LogS:	-4.456
# Rotatable Bonds:	2
TPSA:	61.83
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.569
Synthetic Accessibility Score:	6.39
Fsp3:	0.6
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:	-4.796
MDCK Permeability:	2.5702651328174397e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.959
30% Bioavailability (F30%):	0.688

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.852
Plasma Protein Binding (PPB):	73.73857879638672%
Volume Distribution (VD):	1.593
Pgp-substrate:	37.482120513916016%

ADMET: Metabolism

CYP1A2-inhibitor:	0.035
CYP1A2-substrate:	0.852
CYP2C19-inhibitor:	0.456
CYP2C19-substrate:	0.766
CYP2C9-inhibitor:	0.13
CYP2C9-substrate:	0.047
CYP2D6-inhibitor:	0.092
CYP2D6-substrate:	0.154
CYP3A4-inhibitor:	0.915
CYP3A4-substrate:	0.423

ADMET: Excretion

Clearance (CL):	7.659
Half-life (T1/2):	0.042

ADMET: Toxicity

hERG Blockers:	0.231
Human Hepatotoxicity (H-HT):	0.542
Drug-inuced Liver Injury (DILI):	0.118
AMES Toxicity:	0.82
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.955
Skin Sensitization:	0.88
Carcinogencity:	0.425
Eye Corrosion:	0.101
Eye Irritation:	0.018
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC474899

Natural Product ID:	NPC474899
*Common Name:**	Transtaganolide C
IUPAC Name:	n.a.
Synonyms:	Transtaganolide C
Standard InCHIKey:	WEROHVUUBZUWOZ-MQEXTWSESA-N
Standard InCHI:	InChI=1S/C20H24O5/c1-6-19(4)8-7-13-18(2,3)12-9-11-10-14(23-5)24-17(22)15(19)20(11,13)25-16(12)21/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13-,15-,19+,20+/m0/s1
SMILES:	COC1=CC2=C[C@H]3C(=O)O[C@@]42[C@@H](C(=O)O1)[C@](C)(C=C)CC[C@H]4C3(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL486793
PubChem CID:	44559268
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000086] Pyrans [CHEMONTID:0000481] Pyranones and derivatives [CHEMONTID:0001211] Dihydropyranones

*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
NPO6971	Thapsia garganica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16124763]
NPO6971	Thapsia garganica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO6971	Thapsia garganica	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6971	Thapsia garganica	Species	Apiaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified		Activity	=	65.4	%	PMID[502216]

☑ 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 NPC474899 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	262
0.1-0.2	1447
0.2-0.3	4134
0.3-0.4	7925
0.4-0.5	15696
0.5-0.6	8261
0.6-0.7	4626
0.7-0.8	341
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474912
0.9485	High Similarity	NPC474898
0.9485	High Similarity	NPC476001
0.819	Intermediate Similarity	NPC476958
0.7879	Intermediate Similarity	NPC213636
0.7879	Intermediate Similarity	NPC280592
0.7879	Intermediate Similarity	NPC253177
0.78	Intermediate Similarity	NPC471329
0.78	Intermediate Similarity	NPC296114
0.7736	Intermediate Similarity	NPC132395
0.7736	Intermediate Similarity	NPC471365
0.7736	Intermediate Similarity	NPC471364
0.7699	Intermediate Similarity	NPC476959
0.7677	Intermediate Similarity	NPC472302
0.767	Intermediate Similarity	NPC112654
0.7664	Intermediate Similarity	NPC325769
0.7647	Intermediate Similarity	NPC38830
0.7642	Intermediate Similarity	NPC475091
0.76	Intermediate Similarity	NPC284561
0.7576	Intermediate Similarity	NPC231599
0.7576	Intermediate Similarity	NPC471728
0.757	Intermediate Similarity	NPC476770
0.7547	Intermediate Similarity	NPC168319
0.7547	Intermediate Similarity	NPC194028
0.7525	Intermediate Similarity	NPC469595
0.7525	Intermediate Similarity	NPC212679
0.7525	Intermediate Similarity	NPC220454
0.75	Intermediate Similarity	NPC476764
0.75	Intermediate Similarity	NPC473151
0.75	Intermediate Similarity	NPC4573
0.75	Intermediate Similarity	NPC239162
0.75	Intermediate Similarity	NPC470297
0.75	Intermediate Similarity	NPC478260
0.75	Intermediate Similarity	NPC478261
0.75	Intermediate Similarity	NPC477128
0.75	Intermediate Similarity	NPC277769
0.75	Intermediate Similarity	NPC476763
0.75	Intermediate Similarity	NPC265391
0.75	Intermediate Similarity	NPC478259
0.7477	Intermediate Similarity	NPC478209
0.7476	Intermediate Similarity	NPC470697
0.7476	Intermediate Similarity	NPC477130
0.7476	Intermediate Similarity	NPC477129
0.7453	Intermediate Similarity	NPC474012
0.7453	Intermediate Similarity	NPC476299
0.7451	Intermediate Similarity	NPC36491
0.7431	Intermediate Similarity	NPC266570
0.7431	Intermediate Similarity	NPC476762
0.7431	Intermediate Similarity	NPC476761
0.7431	Intermediate Similarity	NPC476760
0.7429	Intermediate Similarity	NPC38530
0.7429	Intermediate Similarity	NPC2049
0.7429	Intermediate Similarity	NPC110937
0.7429	Intermediate Similarity	NPC84335
0.7429	Intermediate Similarity	NPC476768
0.7426	Intermediate Similarity	NPC173042
0.7426	Intermediate Similarity	NPC50070
0.7407	Intermediate Similarity	NPC475526
0.7407	Intermediate Similarity	NPC291154
0.7407	Intermediate Similarity	NPC329345
0.7407	Intermediate Similarity	NPC473283
0.74	Intermediate Similarity	NPC125925
0.74	Intermediate Similarity	NPC181327
0.74	Intermediate Similarity	NPC171722
0.7391	Intermediate Similarity	NPC243298
0.7387	Intermediate Similarity	NPC137911
0.7387	Intermediate Similarity	NPC228477
0.7358	Intermediate Similarity	NPC316598
0.7353	Intermediate Similarity	NPC8062
0.7353	Intermediate Similarity	NPC327183
0.7353	Intermediate Similarity	NPC469372
0.7353	Intermediate Similarity	NPC328935
0.7345	Intermediate Similarity	NPC90952
0.7333	Intermediate Similarity	NPC311166
0.7327	Intermediate Similarity	NPC24816
0.732	Intermediate Similarity	NPC476101
0.7315	Intermediate Similarity	NPC471993
0.7315	Intermediate Similarity	NPC478156
0.7308	Intermediate Similarity	NPC84893
0.73	Intermediate Similarity	NPC220478
0.73	Intermediate Similarity	NPC470415
0.7297	Intermediate Similarity	NPC475418
0.7297	Intermediate Similarity	NPC473482
0.7297	Intermediate Similarity	NPC318363
0.729	Intermediate Similarity	NPC473204
0.729	Intermediate Similarity	NPC117685
0.7282	Intermediate Similarity	NPC49420
0.7281	Intermediate Similarity	NPC478212
0.7273	Intermediate Similarity	NPC478208
0.7273	Intermediate Similarity	NPC469607
0.7273	Intermediate Similarity	NPC252296
0.7265	Intermediate Similarity	NPC158963
0.7264	Intermediate Similarity	NPC47834
0.7264	Intermediate Similarity	NPC472188
0.7257	Intermediate Similarity	NPC470246
0.7257	Intermediate Similarity	NPC470960
0.7255	Intermediate Similarity	NPC118011
0.7255	Intermediate Similarity	NPC36668
0.7255	Intermediate Similarity	NPC97577
0.725	Intermediate Similarity	NPC32868
0.725	Intermediate Similarity	NPC241456
0.7248	Intermediate Similarity	NPC470954
0.7248	Intermediate Similarity	NPC25666
0.7248	Intermediate Similarity	NPC90177
0.7248	Intermediate Similarity	NPC271059
0.7241	Intermediate Similarity	NPC475809
0.7241	Intermediate Similarity	NPC134430
0.7238	Intermediate Similarity	NPC217329
0.7238	Intermediate Similarity	NPC295347
0.7238	Intermediate Similarity	NPC209355
0.7232	Intermediate Similarity	NPC469370
0.7232	Intermediate Similarity	NPC475065
0.7232	Intermediate Similarity	NPC476759
0.7228	Intermediate Similarity	NPC74139
0.7228	Intermediate Similarity	NPC30421
0.7227	Intermediate Similarity	NPC287236
0.7222	Intermediate Similarity	NPC323441
0.7222	Intermediate Similarity	NPC469657
0.7222	Intermediate Similarity	NPC244456
0.7216	Intermediate Similarity	NPC474978
0.7212	Intermediate Similarity	NPC472303
0.7207	Intermediate Similarity	NPC329048
0.7207	Intermediate Similarity	NPC330011
0.7207	Intermediate Similarity	NPC475570
0.7207	Intermediate Similarity	NPC184512
0.7203	Intermediate Similarity	NPC184555
0.72	Intermediate Similarity	NPC76333
0.72	Intermediate Similarity	NPC248703
0.7196	Intermediate Similarity	NPC472186
0.7196	Intermediate Similarity	NPC476800
0.7196	Intermediate Similarity	NPC318917
0.7196	Intermediate Similarity	NPC64742
0.7196	Intermediate Similarity	NPC471366
0.7193	Intermediate Similarity	NPC222834
0.7184	Intermediate Similarity	NPC223093
0.7179	Intermediate Similarity	NPC471249
0.7179	Intermediate Similarity	NPC284707
0.717	Intermediate Similarity	NPC9812
0.7168	Intermediate Similarity	NPC83005
0.7168	Intermediate Similarity	NPC16270
0.7168	Intermediate Similarity	NPC476766
0.7168	Intermediate Similarity	NPC472666
0.7167	Intermediate Similarity	NPC55602
0.7167	Intermediate Similarity	NPC204812
0.7157	Intermediate Similarity	NPC476427
0.7157	Intermediate Similarity	NPC196407
0.7157	Intermediate Similarity	NPC124927
0.7157	Intermediate Similarity	NPC475101
0.7156	Intermediate Similarity	NPC32577
0.7156	Intermediate Similarity	NPC320447
0.7156	Intermediate Similarity	NPC155332
0.7156	Intermediate Similarity	NPC476769
0.7156	Intermediate Similarity	NPC114540
0.7155	Intermediate Similarity	NPC476963
0.7143	Intermediate Similarity	NPC476802
0.7143	Intermediate Similarity	NPC476765
0.7143	Intermediate Similarity	NPC473807
0.7143	Intermediate Similarity	NPC89171
0.7143	Intermediate Similarity	NPC473431
0.7143	Intermediate Similarity	NPC473280
0.7143	Intermediate Similarity	NPC473435
0.7143	Intermediate Similarity	NPC220155
0.7143	Intermediate Similarity	NPC471078
0.7143	Intermediate Similarity	NPC473483
0.7143	Intermediate Similarity	NPC88507
0.713	Intermediate Similarity	NPC75167
0.713	Intermediate Similarity	NPC54705
0.713	Intermediate Similarity	NPC476933
0.713	Intermediate Similarity	NPC477720
0.713	Intermediate Similarity	NPC474718
0.713	Intermediate Similarity	NPC473545
0.713	Intermediate Similarity	NPC311592
0.713	Intermediate Similarity	NPC73050
0.713	Intermediate Similarity	NPC472187
0.7129	Intermediate Similarity	NPC198314
0.7119	Intermediate Similarity	NPC473636
0.7119	Intermediate Similarity	NPC211093
0.7119	Intermediate Similarity	NPC473839
0.7119	Intermediate Similarity	NPC77689
0.7119	Intermediate Similarity	NPC245320
0.7117	Intermediate Similarity	NPC127609
0.7117	Intermediate Similarity	NPC477125
0.7117	Intermediate Similarity	NPC34768
0.7117	Intermediate Similarity	NPC478052
0.7117	Intermediate Similarity	NPC1679
0.7115	Intermediate Similarity	NPC45579
0.7115	Intermediate Similarity	NPC289479
0.7115	Intermediate Similarity	NPC303697
0.7115	Intermediate Similarity	NPC65513
0.7109	Intermediate Similarity	NPC75616
0.7105	Intermediate Similarity	NPC474315
0.7103	Intermediate Similarity	NPC208094
0.7103	Intermediate Similarity	NPC158347
0.7103	Intermediate Similarity	NPC254496
0.7103	Intermediate Similarity	NPC285513
0.7103	Intermediate Similarity	NPC474977
0.7103	Intermediate Similarity	NPC53844
0.71	Intermediate Similarity	NPC139566
0.7094	Intermediate Similarity	NPC469684
0.7094	Intermediate Similarity	NPC478204

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 NPC474899 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	250
0.1-0.2	1445
0.2-0.3	3591
0.3-0.4	2410
0.4-0.5	1038
0.5-0.6	276
0.6-0.7	138
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
0.7451	Intermediate Similarity	NPD6411	Approved
0.7255	Intermediate Similarity	NPD6101	Approved
0.7255	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD3573	Approved
0.7048	Intermediate Similarity	NPD5779	Approved
0.7048	Intermediate Similarity	NPD5778	Approved
0.69	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8513	Phase 3
0.6807	Remote Similarity	NPD7115	Discovery
0.6721	Remote Similarity	NPD8516	Approved
0.6721	Remote Similarity	NPD8517	Approved
0.6721	Remote Similarity	NPD8515	Approved
0.6701	Remote Similarity	NPD8039	Approved
0.6699	Remote Similarity	NPD1694	Approved
0.6636	Remote Similarity	NPD5694	Approved
0.6636	Remote Similarity	NPD5693	Phase 1
0.6614	Remote Similarity	NPD7319	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.661	Remote Similarity	NPD6882	Approved
0.6585	Remote Similarity	NPD7503	Approved
0.6577	Remote Similarity	NPD4225	Approved
0.6552	Remote Similarity	NPD6686	Approved
0.6552	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6545	Remote Similarity	NPD7839	Suspended
0.6542	Remote Similarity	NPD5692	Phase 3
0.6542	Remote Similarity	NPD5207	Approved
0.6508	Remote Similarity	NPD7507	Approved
0.6481	Remote Similarity	NPD6050	Approved
0.6466	Remote Similarity	NPD5697	Approved
0.6457	Remote Similarity	NPD8074	Phase 3
0.6455	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD7638	Approved
0.641	Remote Similarity	NPD6881	Approved
0.641	Remote Similarity	NPD6899	Approved
0.6379	Remote Similarity	NPD7128	Approved
0.6379	Remote Similarity	NPD5739	Approved
0.6379	Remote Similarity	NPD6402	Approved
0.6379	Remote Similarity	NPD6008	Approved
0.6379	Remote Similarity	NPD6675	Approved
0.6372	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD7640	Approved
0.6364	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD7900	Approved
0.6364	Remote Similarity	NPD7748	Approved
0.6356	Remote Similarity	NPD6014	Approved
0.6356	Remote Similarity	NPD6013	Approved
0.6356	Remote Similarity	NPD6012	Approved
0.6355	Remote Similarity	NPD5737	Approved
0.6355	Remote Similarity	NPD6672	Approved
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5284	Approved
0.633	Remote Similarity	NPD7637	Suspended
0.6325	Remote Similarity	NPD5701	Approved
0.6321	Remote Similarity	NPD6098	Approved
0.6321	Remote Similarity	NPD5330	Approved
0.6321	Remote Similarity	NPD7334	Approved
0.6321	Remote Similarity	NPD7146	Approved
0.6321	Remote Similarity	NPD7521	Approved
0.6321	Remote Similarity	NPD6409	Approved
0.6321	Remote Similarity	NPD6684	Approved
0.6306	Remote Similarity	NPD5695	Phase 3
0.6303	Remote Similarity	NPD7102	Approved
0.6303	Remote Similarity	NPD6883	Approved
0.6303	Remote Similarity	NPD7290	Approved
0.6299	Remote Similarity	NPD7492	Approved
0.6296	Remote Similarity	NPD6673	Approved
0.6296	Remote Similarity	NPD6080	Approved
0.6296	Remote Similarity	NPD6051	Approved
0.6296	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6904	Approved
0.6273	Remote Similarity	NPD6399	Phase 3
0.6271	Remote Similarity	NPD7320	Approved
0.6271	Remote Similarity	NPD6011	Approved
0.626	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6649	Approved
0.625	Remote Similarity	NPD8130	Phase 1
0.625	Remote Similarity	NPD6847	Approved
0.625	Remote Similarity	NPD6616	Approved
0.625	Remote Similarity	NPD5209	Approved
0.625	Remote Similarity	NPD6617	Approved
0.625	Remote Similarity	NPD6869	Approved
0.625	Remote Similarity	NPD6650	Approved
0.624	Remote Similarity	NPD6054	Approved
0.622	Remote Similarity	NPD8328	Phase 3
0.6218	Remote Similarity	NPD6372	Approved
0.6218	Remote Similarity	NPD6373	Approved
0.6216	Remote Similarity	NPD6001	Approved
0.6204	Remote Similarity	NPD5208	Approved
0.6204	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6903	Approved
0.6202	Remote Similarity	NPD7078	Approved
0.6198	Remote Similarity	NPD8297	Approved
0.6195	Remote Similarity	NPD6083	Phase 2
0.6195	Remote Similarity	NPD6084	Phase 2
0.6195	Remote Similarity	NPD7902	Approved
0.619	Remote Similarity	NPD6016	Approved
0.619	Remote Similarity	NPD6015	Approved
0.6186	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD7515	Phase 2
0.6182	Remote Similarity	NPD7983	Approved
0.6168	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD5654	Approved
0.6154	Remote Similarity	NPD7736	Approved
0.6142	Remote Similarity	NPD5988	Approved
0.6142	Remote Similarity	NPD6370	Approved
0.614	Remote Similarity	NPD5696	Approved
0.6129	Remote Similarity	NPD6009	Approved
0.6121	Remote Similarity	NPD5211	Phase 2
0.6116	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD6059	Approved
0.6111	Remote Similarity	NPD6319	Approved
0.6098	Remote Similarity	NPD6010	Discontinued
0.6087	Remote Similarity	NPD4696	Approved
0.6087	Remote Similarity	NPD5285	Approved
0.6087	Remote Similarity	NPD5286	Approved
0.6083	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6077	Remote Similarity	NPD8293	Discontinued
0.6071	Remote Similarity	NPD5282	Discontinued
0.6058	Remote Similarity	NPD4695	Discontinued
0.6053	Remote Similarity	NPD5959	Approved
0.6053	Remote Similarity	NPD4755	Approved
0.6038	Remote Similarity	NPD7154	Phase 3
0.6036	Remote Similarity	NPD6079	Approved
0.6033	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD4623	Approved
0.6019	Remote Similarity	NPD4519	Discontinued
0.6017	Remote Similarity	NPD5141	Approved
0.6016	Remote Similarity	NPD8133	Approved
0.6015	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5328	Approved
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.5984	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5983	Remote Similarity	NPD4633	Approved
0.5983	Remote Similarity	NPD5224	Approved
0.5983	Remote Similarity	NPD5225	Approved
0.5983	Remote Similarity	NPD5226	Approved
0.5981	Remote Similarity	NPD3668	Phase 3
0.5965	Remote Similarity	NPD5221	Approved
0.5965	Remote Similarity	NPD5222	Approved
0.5965	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD7327	Approved
0.5952	Remote Similarity	NPD7328	Approved
0.595	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.5948	Remote Similarity	NPD6648	Approved
0.5948	Remote Similarity	NPD4700	Approved
0.5946	Remote Similarity	NPD5785	Approved
0.5943	Remote Similarity	NPD3667	Approved
0.5938	Remote Similarity	NPD6921	Approved
0.5938	Remote Similarity	NPD8033	Approved
0.5932	Remote Similarity	NPD5174	Approved
0.5932	Remote Similarity	NPD5175	Approved
0.592	Remote Similarity	NPD6274	Approved
0.5917	Remote Similarity	NPD6412	Phase 2
0.5913	Remote Similarity	NPD5173	Approved
0.5906	Remote Similarity	NPD7100	Approved
0.5906	Remote Similarity	NPD7101	Approved
0.5906	Remote Similarity	NPD7516	Approved
0.5902	Remote Similarity	NPD4634	Approved
0.5897	Remote Similarity	NPD5223	Approved
0.5893	Remote Similarity	NPD8034	Phase 2
0.5893	Remote Similarity	NPD8035	Phase 2
0.5887	Remote Similarity	NPD4632	Approved
0.5882	Remote Similarity	NPD5909	Discontinued
0.5878	Remote Similarity	NPD8451	Approved
0.5873	Remote Similarity	NPD6317	Approved
0.5872	Remote Similarity	NPD4694	Approved
0.5872	Remote Similarity	NPD6422	Discontinued
0.5872	Remote Similarity	NPD3618	Phase 1
0.5872	Remote Similarity	NPD5786	Approved
0.5872	Remote Similarity	NPD5280	Approved
0.5859	Remote Similarity	NPD8377	Approved
0.5859	Remote Similarity	NPD8294	Approved
0.5856	Remote Similarity	NPD4753	Phase 2
0.5849	Remote Similarity	NPD1779	Approved
0.5849	Remote Similarity	NPD1780	Approved
0.5847	Remote Similarity	NPD7632	Discontinued
0.5833	Remote Similarity	NPD4786	Approved
0.5833	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD8448	Approved
0.5833	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5827	Remote Similarity	NPD6313	Approved
0.5827	Remote Similarity	NPD6335	Approved
0.5827	Remote Similarity	NPD6314	Approved
0.5826	Remote Similarity	NPD4697	Phase 3
0.5826	Remote Similarity	NPD7732	Phase 3
0.5821	Remote Similarity	NPD8391	Approved
0.5821	Remote Similarity	NPD8392	Approved
0.5821	Remote Similarity	NPD8390	Approved
0.5814	Remote Similarity	NPD8296	Approved
0.5814	Remote Similarity	NPD8335	Approved
0.5814	Remote Similarity	NPD8378	Approved
0.5814	Remote Similarity	NPD8380	Approved
0.5814	Remote Similarity	NPD8379	Approved
0.5804	Remote Similarity	NPD46	Approved
0.5804	Remote Similarity	NPD6698	Approved
0.5794	Remote Similarity	NPD4221	Approved
0.5794	Remote Similarity	NPD4223	Phase 3
0.5794	Remote Similarity	NPD6868	Approved
0.5784	Remote Similarity	NPD4687	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