NPASS Compound

Structure

NPC476001 OpenBabel07101718222D 28 31 0 0 1 0 0 0 0 0999 V2000 -3.3671 1.4321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5837 1.9693 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3619 -1.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7135 3.7370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8341 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6679 0.7329 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8564 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7127 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7127 0.9889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8564 2.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8564 1.4833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7127 -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 0.3547 2.6944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8564 1.4833 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8564 -0.4944 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8564 2.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3508 -1.3508 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7127 0.9889 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8564 -0.4944 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 0.9889 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8564 -1.4833 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7700 2.5711 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8564 -2.2072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7331 3.6080 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3397 -1.3508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3547 2.6944 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 4 25 1 0 0 0 0 5 26 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 21 1 0 0 0 0 12 16 1 1 0 0 0 12 20 1 0 0 0 0 13 20 1 6 0 0 0 13 21 1 0 0 0 0 14 25 1 0 0 0 0 14 27 1 0 0 0 0 15 17 1 0 0 0 0 15 19 1 6 0 0 0 15 21 1 0 0 0 0 16 22 2 0 0 0 0 16 28 1 0 0 0 0 17 23 2 0 0 0 0 17 27 1 0 0 0 0 18 20 1 0 0 0 0 18 24 2 0 0 0 0 18 26 1 0 0 0 0 19 2 1 1 0 0 0 20 3 1 6 0 0 0 21 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	388.15
Volume:	383.259
LogP:	2.113
LogD:	1.254
LogS:	-4.509
# Rotatable Bonds:	4
TPSA:	88.13
# H-Bond Aceptor:	7
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.415
Synthetic Accessibility Score:	6.496
Fsp3:	0.571
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:	-4.965
MDCK Permeability:	1.844076905399561e-05
Pgp-inhibitor:	0.999
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.958
30% Bioavailability (F30%):	0.981

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.931
Plasma Protein Binding (PPB):	54.3748779296875%
Volume Distribution (VD):	1.028
Pgp-substrate:	45.50897979736328%

ADMET: Metabolism

CYP1A2-inhibitor:	0.025
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.196
CYP2C19-substrate:	0.754
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.014
CYP2D6-substrate:	0.137
CYP3A4-inhibitor:	0.933
CYP3A4-substrate:	0.528

ADMET: Excretion

Clearance (CL):	5.707
Half-life (T1/2):	0.184

ADMET: Toxicity

hERG Blockers:	0.336
Human Hepatotoxicity (H-HT):	0.652
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.954
Rat Oral Acute Toxicity:	0.942
Maximum Recommended Daily Dose:	0.92
Skin Sensitization:	0.812
Carcinogencity:	0.617
Eye Corrosion:	0.004
Eye Irritation:	0.011
Respiratory Toxicity:	0.91

Download Data

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

Natural Product: NPC476001

Natural Product ID:	NPC476001
*Common Name:**	Basiliolide B
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	UTAYDCZHINEPNU-APGXBUQOSA-N
Standard InCHI:	InChI=1S/C21H24O7/c1-6-19(2)8-7-13-20(3,18(24)26-5)12-9-11-10-14(25-4)27-17(23)15(19)21(11,13)28-16(12)22/h6,9-10,12-13,15H,1,7-8H2,2-5H3/t12-,13-,15-,19-,20+,21+/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]4[C@]3(C)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521046
PubChem CID:	21593994
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0001986] Tricarboxylic acids and derivatives

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
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	=	61.4	%	PMID[513636]

☑ 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 NPC476001 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	274
0.1-0.2	1484
0.2-0.3	4233
0.3-0.4	8013
0.4-0.5	15316
0.5-0.6	8477
0.6-0.7	4622
0.7-0.8	274
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9794	High Similarity	NPC474898
0.9485	High Similarity	NPC474899
0.9485	High Similarity	NPC474912
0.7963	Intermediate Similarity	NPC476958
0.785	Intermediate Similarity	NPC132395
0.785	Intermediate Similarity	NPC471365
0.785	Intermediate Similarity	NPC471364
0.7822	Intermediate Similarity	NPC280592
0.7822	Intermediate Similarity	NPC213636
0.7822	Intermediate Similarity	NPC253177
0.78	Intermediate Similarity	NPC477128
0.7788	Intermediate Similarity	NPC112654
0.7778	Intermediate Similarity	NPC470297
0.7767	Intermediate Similarity	NPC470697
0.7767	Intermediate Similarity	NPC477129
0.7767	Intermediate Similarity	NPC477130
0.7745	Intermediate Similarity	NPC471329
0.7745	Intermediate Similarity	NPC296114
0.7723	Intermediate Similarity	NPC284561
0.7658	Intermediate Similarity	NPC137911
0.7658	Intermediate Similarity	NPC228477
0.7647	Intermediate Similarity	NPC212679
0.7647	Intermediate Similarity	NPC469595
0.7647	Intermediate Similarity	NPC220454
0.7624	Intermediate Similarity	NPC472302
0.7615	Intermediate Similarity	NPC325769
0.7611	Intermediate Similarity	NPC277769
0.7596	Intermediate Similarity	NPC38830
0.7589	Intermediate Similarity	NPC478209
0.7549	Intermediate Similarity	NPC173042
0.7547	Intermediate Similarity	NPC38530
0.7547	Intermediate Similarity	NPC84335
0.7545	Intermediate Similarity	NPC469607
0.7545	Intermediate Similarity	NPC1679
0.7525	Intermediate Similarity	NPC231599
0.7523	Intermediate Similarity	NPC271059
0.7523	Intermediate Similarity	NPC25666
0.75	Intermediate Similarity	NPC469657
0.75	Intermediate Similarity	NPC469370
0.75	Intermediate Similarity	NPC244456
0.75	Intermediate Similarity	NPC323441
0.75	Intermediate Similarity	NPC476959
0.75	Intermediate Similarity	NPC243298
0.7479	Intermediate Similarity	NPC287236
0.7476	Intermediate Similarity	NPC469372
0.7456	Intermediate Similarity	NPC4573
0.7456	Intermediate Similarity	NPC265391
0.7456	Intermediate Similarity	NPC90952
0.7453	Intermediate Similarity	NPC311166
0.7451	Intermediate Similarity	NPC478260
0.7451	Intermediate Similarity	NPC478259
0.7451	Intermediate Similarity	NPC478261
0.7436	Intermediate Similarity	NPC284707
0.7431	Intermediate Similarity	NPC475091
0.7411	Intermediate Similarity	NPC89171
0.7411	Intermediate Similarity	NPC476802
0.7407	Intermediate Similarity	NPC474012
0.7407	Intermediate Similarity	NPC476299
0.7407	Intermediate Similarity	NPC473204
0.7407	Intermediate Similarity	NPC476933
0.7404	Intermediate Similarity	NPC65513
0.7404	Intermediate Similarity	NPC49420
0.7391	Intermediate Similarity	NPC478212
0.7391	Intermediate Similarity	NPC471204
0.7387	Intermediate Similarity	NPC478208
0.7387	Intermediate Similarity	NPC252296
0.7387	Intermediate Similarity	NPC477125
0.7383	Intermediate Similarity	NPC472188
0.7364	Intermediate Similarity	NPC476770
0.7364	Intermediate Similarity	NPC90177
0.7353	Intermediate Similarity	NPC181327
0.7353	Intermediate Similarity	NPC125925
0.7353	Intermediate Similarity	NPC471728
0.7353	Intermediate Similarity	NPC171722
0.735	Intermediate Similarity	NPC98249
0.735	Intermediate Similarity	NPC469684
0.735	Intermediate Similarity	NPC53396
0.735	Intermediate Similarity	NPC134430
0.7345	Intermediate Similarity	NPC112457
0.7339	Intermediate Similarity	NPC168319
0.7339	Intermediate Similarity	NPC194028
0.7339	Intermediate Similarity	NPC472637
0.7333	Intermediate Similarity	NPC1108
0.7333	Intermediate Similarity	NPC471571
0.7321	Intermediate Similarity	NPC184512
0.7315	Intermediate Similarity	NPC318917
0.7315	Intermediate Similarity	NPC316598
0.7315	Intermediate Similarity	NPC476800
0.7315	Intermediate Similarity	NPC471366
0.7315	Intermediate Similarity	NPC176845
0.7315	Intermediate Similarity	NPC472186
0.7308	Intermediate Similarity	NPC327183
0.7308	Intermediate Similarity	NPC328935
0.7304	Intermediate Similarity	NPC222834
0.7297	Intermediate Similarity	NPC119493
0.7297	Intermediate Similarity	NPC189616
0.7297	Intermediate Similarity	NPC239162
0.729	Intermediate Similarity	NPC269492
0.7288	Intermediate Similarity	NPC471249
0.7282	Intermediate Similarity	NPC24816
0.7273	Intermediate Similarity	NPC476101
0.7273	Intermediate Similarity	NPC273005
0.7273	Intermediate Similarity	NPC31058
0.7273	Intermediate Similarity	NPC469606
0.7273	Intermediate Similarity	NPC478156
0.7265	Intermediate Similarity	NPC477509
0.7264	Intermediate Similarity	NPC476415
0.7264	Intermediate Similarity	NPC88507
0.7255	Intermediate Similarity	NPC220478
0.7248	Intermediate Similarity	NPC473545
0.7248	Intermediate Similarity	NPC472187
0.7248	Intermediate Similarity	NPC174314
0.7238	Intermediate Similarity	NPC36491
0.7232	Intermediate Similarity	NPC34768
0.7232	Intermediate Similarity	NPC266570
0.7232	Intermediate Similarity	NPC472645
0.7232	Intermediate Similarity	NPC478052
0.7227	Intermediate Similarity	NPC77689
0.7227	Intermediate Similarity	NPC158963
0.7227	Intermediate Similarity	NPC245320
0.7227	Intermediate Similarity	NPC473636
0.7222	Intermediate Similarity	NPC2049
0.7222	Intermediate Similarity	NPC257726
0.7222	Intermediate Similarity	NPC476768
0.7222	Intermediate Similarity	NPC110937
0.7222	Intermediate Similarity	NPC204054
0.7222	Intermediate Similarity	NPC285513
0.7222	Intermediate Similarity	NPC254496
0.7217	Intermediate Similarity	NPC304180
0.7217	Intermediate Similarity	NPC179798
0.7217	Intermediate Similarity	NPC470960
0.7217	Intermediate Similarity	NPC474315
0.7213	Intermediate Similarity	NPC241456
0.7213	Intermediate Similarity	NPC32868
0.7212	Intermediate Similarity	NPC50070
0.7212	Intermediate Similarity	NPC118011
0.7212	Intermediate Similarity	NPC36668
0.7207	Intermediate Similarity	NPC291154
0.7207	Intermediate Similarity	NPC475526
0.7207	Intermediate Similarity	NPC329345
0.7207	Intermediate Similarity	NPC320154
0.7207	Intermediate Similarity	NPC134270
0.7207	Intermediate Similarity	NPC473283
0.7207	Intermediate Similarity	NPC254202
0.7203	Intermediate Similarity	NPC475809
0.7203	Intermediate Similarity	NPC23046
0.7203	Intermediate Similarity	NPC478204
0.7196	Intermediate Similarity	NPC471372
0.7196	Intermediate Similarity	NPC217329
0.7196	Intermediate Similarity	NPC473369
0.7196	Intermediate Similarity	NPC471362
0.7196	Intermediate Similarity	NPC295347
0.7196	Intermediate Similarity	NPC472189
0.7193	Intermediate Similarity	NPC478210
0.7193	Intermediate Similarity	NPC220705
0.7182	Intermediate Similarity	NPC473384
0.7172	Intermediate Similarity	NPC195424
0.7172	Intermediate Similarity	NPC474978
0.7168	Intermediate Similarity	NPC180744
0.7168	Intermediate Similarity	NPC133422
0.7167	Intermediate Similarity	NPC31641
0.7167	Intermediate Similarity	NPC473145
0.7165	Intermediate Similarity	NPC248703
0.7157	Intermediate Similarity	NPC76333
0.7155	Intermediate Similarity	NPC269530
0.7155	Intermediate Similarity	NPC476801
0.7143	Intermediate Similarity	NPC214844
0.7143	Intermediate Similarity	NPC473207
0.7143	Intermediate Similarity	NPC223093
0.7143	Intermediate Similarity	NPC108581
0.7143	Intermediate Similarity	NPC478205
0.7143	Intermediate Similarity	NPC81567
0.7143	Intermediate Similarity	NPC118911
0.7143	Intermediate Similarity	NPC476763
0.7143	Intermediate Similarity	NPC8062
0.7143	Intermediate Similarity	NPC76286
0.7143	Intermediate Similarity	NPC478206
0.7143	Intermediate Similarity	NPC152467
0.7143	Intermediate Similarity	NPC201880
0.7143	Intermediate Similarity	NPC470321
0.7143	Intermediate Similarity	NPC476764
0.7143	Intermediate Similarity	NPC264867
0.7131	Intermediate Similarity	NPC204812
0.713	Intermediate Similarity	NPC253906
0.713	Intermediate Similarity	NPC83005
0.713	Intermediate Similarity	NPC119550
0.713	Intermediate Similarity	NPC478211
0.713	Intermediate Similarity	NPC472666
0.713	Intermediate Similarity	NPC260796
0.713	Intermediate Similarity	NPC171598
0.712	Intermediate Similarity	NPC221414
0.7119	Intermediate Similarity	NPC64318
0.7117	Intermediate Similarity	NPC80781
0.7117	Intermediate Similarity	NPC471363
0.7117	Intermediate Similarity	NPC471993
0.7117	Intermediate Similarity	NPC238397
0.7117	Intermediate Similarity	NPC235369
0.7115	Intermediate Similarity	NPC473151
0.7115	Intermediate Similarity	NPC215831
0.7115	Intermediate Similarity	NPC196407

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 NPC476001 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	259
0.1-0.2	1463
0.2-0.3	3669
0.3-0.4	2377
0.4-0.5	985
0.5-0.6	263
0.6-0.7	133
0.7-0.8	1
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
0.7238	Intermediate Similarity	NPD6411	Approved
0.7048	Intermediate Similarity	NPD5764	Clinical (unspecified phase)
0.7048	Intermediate Similarity	NPD6101	Approved
0.7019	Intermediate Similarity	NPD3573	Approved
0.7009	Intermediate Similarity	NPD5779	Approved
0.7009	Intermediate Similarity	NPD5778	Approved
0.6967	Remote Similarity	NPD8513	Phase 3
0.6917	Remote Similarity	NPD7115	Discovery
0.6829	Remote Similarity	NPD8517	Approved
0.6829	Remote Similarity	NPD8515	Approved
0.6829	Remote Similarity	NPD8516	Approved
0.6827	Remote Similarity	NPD1694	Approved
0.6789	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6789	Remote Similarity	NPD7900	Approved
0.6723	Remote Similarity	NPD6882	Approved
0.6723	Remote Similarity	NPD6053	Discontinued
0.6699	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6697	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5207	Approved
0.6667	Remote Similarity	NPD8039	Approved
0.6639	Remote Similarity	NPD6649	Approved
0.6639	Remote Similarity	NPD6650	Approved
0.6638	Remote Similarity	NPD6008	Approved
0.661	Remote Similarity	NPD6372	Approved
0.661	Remote Similarity	NPD6373	Approved
0.6607	Remote Similarity	NPD7902	Approved
0.6606	Remote Similarity	NPD5284	Approved
0.6606	Remote Similarity	NPD5281	Approved
0.6606	Remote Similarity	NPD5693	Phase 1
0.6606	Remote Similarity	NPD5694	Approved
0.6581	Remote Similarity	NPD5697	Approved
0.6581	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD8074	Phase 3
0.656	Remote Similarity	NPD7503	Approved
0.6549	Remote Similarity	NPD4225	Approved
0.6525	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6525	Remote Similarity	NPD6881	Approved
0.6525	Remote Similarity	NPD6899	Approved
0.6514	Remote Similarity	NPD5692	Phase 3
0.6496	Remote Similarity	NPD5739	Approved
0.6496	Remote Similarity	NPD6675	Approved
0.6496	Remote Similarity	NPD6402	Approved
0.6496	Remote Similarity	NPD7128	Approved
0.6471	Remote Similarity	NPD6013	Approved
0.6471	Remote Similarity	NPD6014	Approved
0.6471	Remote Similarity	NPD6012	Approved
0.6462	Remote Similarity	NPD7319	Approved
0.6455	Remote Similarity	NPD6050	Approved
0.6441	Remote Similarity	NPD5701	Approved
0.6417	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD7290	Approved
0.6417	Remote Similarity	NPD6883	Approved
0.6417	Remote Similarity	NPD7102	Approved
0.6406	Remote Similarity	NPD7492	Approved
0.6387	Remote Similarity	NPD6686	Approved
0.6387	Remote Similarity	NPD7320	Approved
0.6387	Remote Similarity	NPD6011	Approved
0.6371	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6617	Approved
0.6364	Remote Similarity	NPD6847	Approved
0.6364	Remote Similarity	NPD8130	Phase 1
0.6364	Remote Similarity	NPD6869	Approved
0.6357	Remote Similarity	NPD7507	Approved
0.6357	Remote Similarity	NPD6616	Approved
0.6349	Remote Similarity	NPD6054	Approved
0.6339	Remote Similarity	NPD7748	Approved
0.6339	Remote Similarity	NPD6001	Approved
0.633	Remote Similarity	NPD6672	Approved
0.633	Remote Similarity	NPD5737	Approved
0.6328	Remote Similarity	NPD8328	Phase 3
0.6311	Remote Similarity	NPD8297	Approved
0.6308	Remote Similarity	NPD7078	Approved
0.6299	Remote Similarity	NPD6015	Approved
0.6299	Remote Similarity	NPD6016	Approved
0.6296	Remote Similarity	NPD7146	Approved
0.6296	Remote Similarity	NPD6409	Approved
0.6296	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD7334	Approved
0.6296	Remote Similarity	NPD6684	Approved
0.6296	Remote Similarity	NPD5330	Approved
0.6296	Remote Similarity	NPD6098	Approved
0.6296	Remote Similarity	NPD7521	Approved
0.6283	Remote Similarity	NPD5695	Phase 3
0.6273	Remote Similarity	NPD6080	Approved
0.6273	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD6904	Approved
0.6273	Remote Similarity	NPD6051	Approved
0.6273	Remote Similarity	NPD6673	Approved
0.6261	Remote Similarity	NPD5696	Approved
0.6261	Remote Similarity	NPD7638	Approved
0.626	Remote Similarity	NPD7736	Approved
0.625	Remote Similarity	NPD5988	Approved
0.625	Remote Similarity	NPD6370	Approved
0.624	Remote Similarity	NPD6009	Approved
0.6239	Remote Similarity	NPD5211	Phase 2
0.6228	Remote Similarity	NPD7839	Suspended
0.622	Remote Similarity	NPD6059	Approved
0.622	Remote Similarity	NPD6319	Approved
0.6207	Remote Similarity	NPD5286	Approved
0.6207	Remote Similarity	NPD7639	Approved
0.6207	Remote Similarity	NPD4696	Approved
0.6207	Remote Similarity	NPD7640	Approved
0.6207	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6198	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD8293	Discontinued
0.6182	Remote Similarity	NPD6903	Approved
0.6182	Remote Similarity	NPD5208	Approved
0.6182	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6174	Remote Similarity	NPD6084	Phase 2
0.6174	Remote Similarity	NPD4755	Approved
0.6174	Remote Similarity	NPD6083	Phase 2
0.6161	Remote Similarity	NPD7637	Suspended
0.6161	Remote Similarity	NPD8034	Phase 2
0.6161	Remote Similarity	NPD8035	Phase 2
0.6161	Remote Similarity	NPD7983	Approved
0.6161	Remote Similarity	NPD7515	Phase 2
0.614	Remote Similarity	NPD5654	Approved
0.6134	Remote Similarity	NPD5141	Approved
0.6121	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD7260	Phase 2
0.6102	Remote Similarity	NPD5224	Approved
0.6102	Remote Similarity	NPD5225	Approved
0.6102	Remote Similarity	NPD4633	Approved
0.6102	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD4697	Phase 3
0.6075	Remote Similarity	NPD5209	Approved
0.6068	Remote Similarity	NPD4700	Approved
0.6053	Remote Similarity	NPD5282	Discontinued
0.605	Remote Similarity	NPD5174	Approved
0.605	Remote Similarity	NPD5175	Approved
0.6038	Remote Similarity	NPD4695	Discontinued
0.6034	Remote Similarity	NPD5959	Approved
0.6032	Remote Similarity	NPD6274	Approved
0.6018	Remote Similarity	NPD6079	Approved
0.6017	Remote Similarity	NPD5223	Approved
0.6016	Remote Similarity	NPD4634	Approved
0.6016	Remote Similarity	NPD7100	Approved
0.6016	Remote Similarity	NPD7101	Approved
0.6	Remote Similarity	NPD5786	Approved
0.6	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD4623	Approved
0.5984	Remote Similarity	NPD6317	Approved
0.5982	Remote Similarity	NPD5328	Approved
0.5963	Remote Similarity	NPD3668	Phase 3
0.5952	Remote Similarity	NPD6010	Discontinued
0.5948	Remote Similarity	NPD5222	Approved
0.5948	Remote Similarity	NPD5221	Approved
0.5948	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD6335	Approved
0.5938	Remote Similarity	NPD6314	Approved
0.5938	Remote Similarity	NPD6313	Approved
0.5932	Remote Similarity	NPD6648	Approved
0.5929	Remote Similarity	NPD5785	Approved
0.5926	Remote Similarity	NPD3667	Approved
0.5923	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.5923	Remote Similarity	NPD6921	Approved
0.5902	Remote Similarity	NPD6412	Phase 2
0.5897	Remote Similarity	NPD5173	Approved
0.5887	Remote Similarity	NPD6371	Approved
0.5873	Remote Similarity	NPD8133	Approved
0.5872	Remote Similarity	NPD7154	Phase 3
0.5865	Remote Similarity	NPD8451	Approved
0.5862	Remote Similarity	NPD4629	Approved
0.5862	Remote Similarity	NPD5210	Approved
0.5856	Remote Similarity	NPD4694	Approved
0.5856	Remote Similarity	NPD5280	Approved
0.5854	Remote Similarity	NPD4729	Approved
0.5854	Remote Similarity	NPD4730	Approved
0.5841	Remote Similarity	NPD4753	Phase 2
0.5841	Remote Similarity	NPD1695	Approved
0.5833	Remote Similarity	NPD1780	Approved
0.5833	Remote Similarity	NPD1779	Approved
0.5826	Remote Similarity	NPD4202	Approved
0.5821	Remote Similarity	NPD8448	Approved
0.582	Remote Similarity	NPD4768	Approved
0.582	Remote Similarity	NPD4767	Approved
0.5818	Remote Similarity	NPD4786	Approved
0.5818	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.5814	Remote Similarity	NPD7328	Approved
0.5814	Remote Similarity	NPD7327	Approved
0.5812	Remote Similarity	NPD7732	Phase 3
0.5809	Remote Similarity	NPD8392	Approved
0.5809	Remote Similarity	NPD8390	Approved
0.5809	Remote Similarity	NPD8391	Approved
0.5802	Remote Similarity	NPD6908	Approved
0.5802	Remote Similarity	NPD5983	Phase 2
0.5802	Remote Similarity	NPD6909	Approved
0.5802	Remote Similarity	NPD8033	Approved
0.5786	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.5785	Remote Similarity	NPD4754	Approved
0.5785	Remote Similarity	NPD6052	Approved
0.5781	Remote Similarity	NPD6868	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