NPASS Compound

Structure

NPC473384 OpenBabel07101719242D 25 27 0 0 1 0 0 0 0 0999 V2000 4.2003 -1.2083 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3898 0.4424 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4038 1.2745 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3755 0.9895 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5533 3.5516 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8654 -0.2188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0811 0.1218 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.9593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8185 -0.3282 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5112 0.3212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1958 1.7602 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2511 2.6412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9593 -0.9593 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4837 0.6613 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2806 -0.4481 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5306 0.7707 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.2840 0.1032 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9593 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.1860 2.6402 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.3115 2.4477 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0549 1.4319 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1488 1.6508 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8885 1.9242 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4826 -0.1737 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 9 1 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 11 1 0 0 0 0 5 12 1 0 0 0 0 6 9 2 0 0 0 0 6 15 1 0 0 0 0 7 10 2 0 0 0 0 8 13 1 0 0 0 0 8 14 1 0 0 0 0 10 13 1 0 0 0 0 11 20 2 0 0 0 0 11 23 1 0 0 0 0 12 21 2 0 0 0 0 12 24 1 0 0 0 0 13 19 1 1 0 0 0 14 16 1 0 0 0 0 14 19 1 1 0 0 0 15 17 1 0 0 0 0 15 22 2 0 0 0 0 16 7 1 1 0 0 0 16 25 1 0 0 0 0 17 23 1 0 0 0 0 18 19 1 1 0 0 0 18 24 1 0 0 0 0 18 25 1 0 0 0 0 19 17 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	348.16
Volume:	351.07
LogP:	2.491
LogD:	1.499
LogS:	-3.958
# Rotatable Bonds:	7
TPSA:	78.9
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.431
Synthetic Accessibility Score:	6.046
Fsp3:	0.632
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.049
MDCK Permeability:	5.906301157665439e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.187
20% Bioavailability (F20%):	0.067
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.549
Plasma Protein Binding (PPB):	52.532249450683594%
Volume Distribution (VD):	1.697
Pgp-substrate:	29.25542640686035%

ADMET: Metabolism

CYP1A2-inhibitor:	0.259
CYP1A2-substrate:	0.134
CYP2C19-inhibitor:	0.251
CYP2C19-substrate:	0.635
CYP2C9-inhibitor:	0.182
CYP2C9-substrate:	0.048
CYP2D6-inhibitor:	0.079
CYP2D6-substrate:	0.218
CYP3A4-inhibitor:	0.149
CYP3A4-substrate:	0.445

ADMET: Excretion

Clearance (CL):	2.625
Half-life (T1/2):	0.673

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.69
Drug-inuced Liver Injury (DILI):	0.869
AMES Toxicity:	0.226
Rat Oral Acute Toxicity:	0.11
Maximum Recommended Daily Dose:	0.056
Skin Sensitization:	0.385
Carcinogencity:	0.061
Eye Corrosion:	0.931
Eye Irritation:	0.919
Respiratory Toxicity:	0.825

Download Data

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

Natural Product: NPC473384

Natural Product ID:	NPC473384
*Common Name:**	Clavigerin A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	QFUYTTKICOKMGU-SOCVJYSZSA-N
Standard InCHI:	InChI=1S/C19H24O6/c1-9(2)6-15(22)17(23-11(4)20)19-13-8-14(19)16(7-10(13)3)25-18(19)24-12(5)21/h6-7,13-14,16-18H,8H2,1-5H3/t13-,14+,16-,17?,18+,19+/m1/s1
SMILES:	CC1=CC2C3CC1C3(C(O2)OC(=O)C)C(C(=O)C=C(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL404392
PubChem CID:	44448137
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001549] Monoterpenoids [CHEMONTID:0001564] Bicyclic monoterpenoids

*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
NPO25378	Lepidolaena clavigera	Species	Lepidolaenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18232639]
NPO25378	Lepidolaena clavigera	Species	Lepidolaenaceae	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	3

Activity Type	# Activity
ORGANISM	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT610	Others	Molecular identity unknown		Activity	=	2.0	%	PMID[542029]
NPT21294	ORGANISM	Tineola bisselliella	Tineola bisselliella	Survival	=	95.0	%	PMID[542029]
NPT27	Others	Unspecified		IZ	=	1.0	mm	PMID[542029]

☑ 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 NPC473384 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	244
0.1-0.2	1542
0.2-0.3	5865
0.3-0.4	12490
0.4-0.5	11350
0.5-0.6	7062
0.6-0.7	3733
0.7-0.8	397
0.8-0.85	10
0.85-0.9	1
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9462	High Similarity	NPC473369
0.9247	High Similarity	NPC471571
0.8925	High Similarity	NPC174765
0.8614	High Similarity	NPC132395
0.8614	High Similarity	NPC471365
0.8614	High Similarity	NPC471364
0.8542	High Similarity	NPC65513
0.8384	Intermediate Similarity	NPC112654
0.8265	Intermediate Similarity	NPC476598
0.8265	Intermediate Similarity	NPC476597
0.8235	Intermediate Similarity	NPC472643
0.8182	Intermediate Similarity	NPC476596
0.8119	Intermediate Similarity	NPC204054
0.8119	Intermediate Similarity	NPC257726
0.8095	Intermediate Similarity	NPC472645
0.8085	Intermediate Similarity	NPC193198
0.8037	Intermediate Similarity	NPC112457
0.8021	Intermediate Similarity	NPC220478
0.8	Intermediate Similarity	NPC474359
0.798	Intermediate Similarity	NPC141831
0.7961	Intermediate Similarity	NPC472644
0.7941	Intermediate Similarity	NPC69385
0.79	Intermediate Similarity	NPC166346
0.7879	Intermediate Similarity	NPC212679
0.7879	Intermediate Similarity	NPC220454
0.7879	Intermediate Similarity	NPC281942
0.7879	Intermediate Similarity	NPC152467
0.7879	Intermediate Similarity	NPC232426
0.7879	Intermediate Similarity	NPC471818
0.7879	Intermediate Similarity	NPC469595
0.7864	Intermediate Similarity	NPC222011
0.7864	Intermediate Similarity	NPC54843
0.7857	Intermediate Similarity	NPC226863
0.7857	Intermediate Similarity	NPC23046
0.7857	Intermediate Similarity	NPC477128
0.7843	Intermediate Similarity	NPC311166
0.7822	Intermediate Similarity	NPC477130
0.7822	Intermediate Similarity	NPC148463
0.7822	Intermediate Similarity	NPC477129
0.7812	Intermediate Similarity	NPC469569
0.7812	Intermediate Similarity	NPC71626
0.781	Intermediate Similarity	NPC134077
0.78	Intermediate Similarity	NPC219874
0.7778	Intermediate Similarity	NPC284561
0.7748	Intermediate Similarity	NPC157441
0.7745	Intermediate Similarity	NPC470978
0.7745	Intermediate Similarity	NPC470974
0.7736	Intermediate Similarity	NPC472747
0.7736	Intermediate Similarity	NPC472750
0.7732	Intermediate Similarity	NPC300985
0.7732	Intermediate Similarity	NPC110405
0.7732	Intermediate Similarity	NPC189311
0.7723	Intermediate Similarity	NPC475657
0.7719	Intermediate Similarity	NPC158963
0.7714	Intermediate Similarity	NPC63249
0.7708	Intermediate Similarity	NPC22611
0.7708	Intermediate Similarity	NPC474703
0.7708	Intermediate Similarity	NPC222358
0.77	Intermediate Similarity	NPC469372
0.7692	Intermediate Similarity	NPC176845
0.7677	Intermediate Similarity	NPC196407
0.7677	Intermediate Similarity	NPC215831
0.7664	Intermediate Similarity	NPC472748
0.7658	Intermediate Similarity	NPC222834
0.7658	Intermediate Similarity	NPC12046
0.7658	Intermediate Similarity	NPC194951
0.7647	Intermediate Similarity	NPC88507
0.7647	Intermediate Similarity	NPC470697
0.7647	Intermediate Similarity	NPC474554
0.7636	Intermediate Similarity	NPC5103
0.7629	Intermediate Similarity	NPC159635
0.7624	Intermediate Similarity	NPC150978
0.7624	Intermediate Similarity	NPC74103
0.7624	Intermediate Similarity	NPC284185
0.7624	Intermediate Similarity	NPC123177
0.7624	Intermediate Similarity	NPC165904
0.7624	Intermediate Similarity	NPC70595
0.7624	Intermediate Similarity	NPC179517
0.7619	Intermediate Similarity	NPC470761
0.7619	Intermediate Similarity	NPC469402
0.7619	Intermediate Similarity	NPC473219
0.7615	Intermediate Similarity	NPC476479
0.76	Intermediate Similarity	NPC73995
0.76	Intermediate Similarity	NPC293044
0.7596	Intermediate Similarity	NPC76266
0.7596	Intermediate Similarity	NPC38530
0.7596	Intermediate Similarity	NPC474343
0.7596	Intermediate Similarity	NPC472188
0.7596	Intermediate Similarity	NPC84335
0.7593	Intermediate Similarity	NPC472749
0.7593	Intermediate Similarity	NPC127790
0.7593	Intermediate Similarity	NPC472751
0.7593	Intermediate Similarity	NPC477125
0.7593	Intermediate Similarity	NPC469401
0.7579	Intermediate Similarity	NPC195424
0.7576	Intermediate Similarity	NPC312561
0.7573	Intermediate Similarity	NPC295347
0.757	Intermediate Similarity	NPC254202
0.7568	Intermediate Similarity	NPC304180
0.7568	Intermediate Similarity	NPC179798
0.7553	Intermediate Similarity	NPC471220
0.7551	Intermediate Similarity	NPC472442
0.7551	Intermediate Similarity	NPC78089
0.7549	Intermediate Similarity	NPC109414
0.7544	Intermediate Similarity	NPC243298
0.7526	Intermediate Similarity	NPC472440
0.7525	Intermediate Similarity	NPC253144
0.7524	Intermediate Similarity	NPC473154
0.7524	Intermediate Similarity	NPC476800
0.7524	Intermediate Similarity	NPC472186
0.7524	Intermediate Similarity	NPC471366
0.7524	Intermediate Similarity	NPC318917
0.7524	Intermediate Similarity	NPC23364
0.75	Intermediate Similarity	NPC469628
0.75	Intermediate Similarity	NPC281949
0.75	Intermediate Similarity	NPC469631
0.75	Intermediate Similarity	NPC301477
0.75	Intermediate Similarity	NPC107338
0.75	Intermediate Similarity	NPC471047
0.75	Intermediate Similarity	NPC119493
0.75	Intermediate Similarity	NPC25684
0.75	Intermediate Similarity	NPC475902
0.75	Intermediate Similarity	NPC469653
0.75	Intermediate Similarity	NPC17578
0.75	Intermediate Similarity	NPC240673
0.75	Intermediate Similarity	NPC109607
0.75	Intermediate Similarity	NPC475906
0.75	Intermediate Similarity	NPC258532
0.75	Intermediate Similarity	NPC149237
0.7477	Intermediate Similarity	NPC253906
0.7477	Intermediate Similarity	NPC206595
0.7477	Intermediate Similarity	NPC235014
0.7476	Intermediate Similarity	NPC53685
0.7475	Intermediate Similarity	NPC107787
0.7474	Intermediate Similarity	NPC471299
0.7455	Intermediate Similarity	NPC473288
0.7453	Intermediate Similarity	NPC472187
0.7453	Intermediate Similarity	NPC473545
0.7453	Intermediate Similarity	NPC473204
0.7451	Intermediate Similarity	NPC20713
0.7451	Intermediate Similarity	NPC474631
0.7449	Intermediate Similarity	NPC149869
0.7447	Intermediate Similarity	NPC187568
0.7447	Intermediate Similarity	NPC41780
0.7436	Intermediate Similarity	NPC204731
0.7436	Intermediate Similarity	NPC473250
0.7434	Intermediate Similarity	NPC56448
0.7434	Intermediate Similarity	NPC469454
0.7434	Intermediate Similarity	NPC469496
0.7434	Intermediate Similarity	NPC469463
0.7431	Intermediate Similarity	NPC252296
0.7431	Intermediate Similarity	NPC1679
0.7431	Intermediate Similarity	NPC469607
0.7429	Intermediate Similarity	NPC475709
0.7429	Intermediate Similarity	NPC208094
0.7429	Intermediate Similarity	NPC476768
0.7426	Intermediate Similarity	NPC168131
0.7426	Intermediate Similarity	NPC280833
0.7426	Intermediate Similarity	NPC470734
0.7426	Intermediate Similarity	NPC5509
0.7423	Intermediate Similarity	NPC178676
0.7423	Intermediate Similarity	NPC186276
0.7414	Intermediate Similarity	NPC476529
0.7414	Intermediate Similarity	NPC475775
0.7407	Intermediate Similarity	NPC474166
0.7407	Intermediate Similarity	NPC19239
0.7407	Intermediate Similarity	NPC271059
0.7407	Intermediate Similarity	NPC25666
0.7407	Intermediate Similarity	NPC151516
0.7404	Intermediate Similarity	NPC472189
0.7404	Intermediate Similarity	NPC316215
0.7404	Intermediate Similarity	NPC183012
0.7404	Intermediate Similarity	NPC471362
0.7404	Intermediate Similarity	NPC471372
0.7396	Intermediate Similarity	NPC304795
0.7387	Intermediate Similarity	NPC469370
0.7383	Intermediate Similarity	NPC476478
0.7383	Intermediate Similarity	NPC244456
0.7383	Intermediate Similarity	NPC472753
0.7383	Intermediate Similarity	NPC310981
0.7383	Intermediate Similarity	NPC469657
0.7379	Intermediate Similarity	NPC470576
0.7379	Intermediate Similarity	NPC477615
0.7377	Intermediate Similarity	NPC213634
0.7374	Intermediate Similarity	NPC177932
0.7374	Intermediate Similarity	NPC161957
0.7373	Intermediate Similarity	NPC473231
0.7364	Intermediate Similarity	NPC184512
0.7364	Intermediate Similarity	NPC475294
0.7358	Intermediate Similarity	NPC279561
0.7358	Intermediate Similarity	NPC141191
0.7358	Intermediate Similarity	NPC264378
0.7353	Intermediate Similarity	NPC329857
0.7353	Intermediate Similarity	NPC477782
0.7353	Intermediate Similarity	NPC469718
0.7347	Intermediate Similarity	NPC469
0.7347	Intermediate Similarity	NPC12283
0.7347	Intermediate Similarity	NPC474193
0.7345	Intermediate Similarity	NPC100267
0.7345	Intermediate Similarity	NPC475524

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 NPC473384 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	2059
0.2-0.3	3881
0.3-0.4	2038
0.4-0.5	593
0.5-0.6	247
0.6-0.7	106
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
0.7374	Intermediate Similarity	NPD1694	Approved
0.7327	Intermediate Similarity	NPD5737	Approved
0.7327	Intermediate Similarity	NPD6672	Approved
0.7282	Intermediate Similarity	NPD5693	Phase 1
0.7245	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6882	Approved
0.7143	Intermediate Similarity	NPD6686	Approved
0.7117	Intermediate Similarity	NPD6675	Approved
0.7117	Intermediate Similarity	NPD7128	Approved
0.7117	Intermediate Similarity	NPD5739	Approved
0.7117	Intermediate Similarity	NPD6402	Approved
0.708	Intermediate Similarity	NPD6373	Approved
0.708	Intermediate Similarity	NPD6372	Approved
0.7075	Intermediate Similarity	NPD5695	Phase 3
0.7054	Intermediate Similarity	NPD5697	Approved
0.7054	Intermediate Similarity	NPD5701	Approved
0.7037	Intermediate Similarity	NPD5696	Approved
0.6991	Remote Similarity	NPD7320	Approved
0.6991	Remote Similarity	NPD6899	Approved
0.6991	Remote Similarity	NPD6881	Approved
0.6964	Remote Similarity	NPD6008	Approved
0.6961	Remote Similarity	NPD7334	Approved
0.6961	Remote Similarity	NPD6684	Approved
0.6961	Remote Similarity	NPD7146	Approved
0.6961	Remote Similarity	NPD5330	Approved
0.6961	Remote Similarity	NPD7521	Approved
0.6961	Remote Similarity	NPD6409	Approved
0.6957	Remote Similarity	NPD6650	Approved
0.6957	Remote Similarity	NPD6649	Approved
0.6944	Remote Similarity	NPD6084	Phase 2
0.6944	Remote Similarity	NPD6083	Phase 2
0.693	Remote Similarity	NPD6012	Approved
0.693	Remote Similarity	NPD6014	Approved
0.693	Remote Similarity	NPD6013	Approved
0.6923	Remote Similarity	NPD6673	Approved
0.6923	Remote Similarity	NPD6080	Approved
0.6923	Remote Similarity	NPD6904	Approved
0.6887	Remote Similarity	NPD6399	Phase 3
0.6885	Remote Similarity	NPD8328	Phase 3
0.687	Remote Similarity	NPD6883	Approved
0.687	Remote Similarity	NPD7290	Approved
0.687	Remote Similarity	NPD7102	Approved
0.6857	Remote Similarity	NPD5692	Phase 3
0.6855	Remote Similarity	NPD8293	Discontinued
0.6842	Remote Similarity	NPD6011	Approved
0.6827	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD6903	Approved
0.6822	Remote Similarity	NPD7900	Approved
0.6822	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.681	Remote Similarity	NPD6847	Approved
0.681	Remote Similarity	NPD6869	Approved
0.681	Remote Similarity	NPD8130	Phase 1
0.681	Remote Similarity	NPD6617	Approved
0.6803	Remote Similarity	NPD6370	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6792	Remote Similarity	NPD6050	Approved
0.6792	Remote Similarity	NPD5694	Approved
0.6765	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6754	Remote Similarity	NPD6412	Phase 2
0.6752	Remote Similarity	NPD8297	Approved
0.6727	Remote Similarity	NPD4225	Approved
0.6694	Remote Similarity	NPD7492	Approved
0.6667	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5282	Discontinued
0.6667	Remote Similarity	NPD6009	Approved
0.664	Remote Similarity	NPD6616	Approved
0.664	Remote Similarity	NPD7507	Approved
0.6639	Remote Similarity	NPD6059	Approved
0.6639	Remote Similarity	NPD6054	Approved
0.6636	Remote Similarity	NPD7902	Approved
0.6636	Remote Similarity	NPD4755	Approved
0.6635	Remote Similarity	NPD6098	Approved
0.661	Remote Similarity	NPD6053	Discontinued
0.6606	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD7078	Approved
0.6585	Remote Similarity	NPD6015	Approved
0.6585	Remote Similarity	NPD6016	Approved
0.6583	Remote Similarity	NPD6274	Approved
0.6571	Remote Similarity	NPD3573	Approved
0.6549	Remote Similarity	NPD5211	Phase 2
0.6545	Remote Similarity	NPD4697	Phase 3
0.6542	Remote Similarity	NPD5785	Approved
0.6542	Remote Similarity	NPD5207	Approved
0.6538	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD5988	Approved
0.6531	Remote Similarity	NPD8039	Approved
0.6529	Remote Similarity	NPD7115	Discovery
0.6529	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6518	Remote Similarity	NPD5285	Approved
0.6518	Remote Similarity	NPD5286	Approved
0.6518	Remote Similarity	NPD4700	Approved
0.6518	Remote Similarity	NPD4696	Approved
0.6514	Remote Similarity	NPD7748	Approved
0.6484	Remote Similarity	NPD7319	Approved
0.6481	Remote Similarity	NPD6411	Approved
0.6466	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6455	Remote Similarity	NPD5654	Approved
0.6452	Remote Similarity	NPD8513	Phase 3
0.6452	Remote Similarity	NPD8515	Approved
0.6452	Remote Similarity	NPD8516	Approved
0.6452	Remote Similarity	NPD8517	Approved
0.6449	Remote Similarity	NPD4753	Phase 2
0.6449	Remote Similarity	NPD1695	Approved
0.6435	Remote Similarity	NPD5141	Approved
0.6429	Remote Similarity	NPD7638	Approved
0.6423	Remote Similarity	NPD7100	Approved
0.6423	Remote Similarity	NPD7101	Approved
0.6422	Remote Similarity	NPD5779	Approved
0.6422	Remote Similarity	NPD5778	Approved
0.6408	Remote Similarity	NPD5209	Approved
0.6404	Remote Similarity	NPD5224	Approved
0.6404	Remote Similarity	NPD4633	Approved
0.6404	Remote Similarity	NPD5225	Approved
0.6404	Remote Similarity	NPD5226	Approved
0.6396	Remote Similarity	NPD5222	Approved
0.6396	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6393	Remote Similarity	NPD6317	Approved
0.6389	Remote Similarity	NPD46	Approved
0.6389	Remote Similarity	NPD6698	Approved
0.6387	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6385	Remote Similarity	NPD7260	Phase 2
0.6373	Remote Similarity	NPD4695	Discontinued
0.6372	Remote Similarity	NPD7639	Approved
0.6372	Remote Similarity	NPD7640	Approved
0.6371	Remote Similarity	NPD6319	Approved
0.6364	Remote Similarity	NPD6001	Approved
0.6355	Remote Similarity	NPD5208	Approved
0.6348	Remote Similarity	NPD5174	Approved
0.6348	Remote Similarity	NPD5175	Approved
0.6341	Remote Similarity	NPD6313	Approved
0.6341	Remote Similarity	NPD6335	Approved
0.6341	Remote Similarity	NPD6314	Approved
0.6339	Remote Similarity	NPD5173	Approved
0.6339	Remote Similarity	NPD5959	Approved
0.633	Remote Similarity	NPD7515	Phase 2
0.633	Remote Similarity	NPD5281	Approved
0.633	Remote Similarity	NPD5284	Approved
0.6321	Remote Similarity	NPD5279	Phase 3
0.6321	Remote Similarity	NPD3618	Phase 1
0.632	Remote Similarity	NPD6908	Approved
0.632	Remote Similarity	NPD6909	Approved
0.632	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD5223	Approved
0.6311	Remote Similarity	NPD6868	Approved
0.6306	Remote Similarity	NPD4629	Approved
0.6306	Remote Similarity	NPD5210	Approved
0.6303	Remote Similarity	NPD6371	Approved
0.6303	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD6101	Approved
0.6296	Remote Similarity	NPD6051	Approved
0.6296	Remote Similarity	NPD5328	Approved
0.6296	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD3133	Approved
0.6286	Remote Similarity	NPD3668	Phase 3
0.6286	Remote Similarity	NPD3665	Phase 1
0.6286	Remote Similarity	NPD3666	Approved
0.6281	Remote Similarity	NPD4632	Approved
0.625	Remote Similarity	NPD6435	Approved
0.625	Remote Similarity	NPD3667	Approved
0.6239	Remote Similarity	NPD4768	Approved
0.6239	Remote Similarity	NPD4767	Approved
0.6218	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6212	Remote Similarity	NPD6845	Suspended
0.6207	Remote Similarity	NPD4754	Approved
0.619	Remote Similarity	NPD5983	Phase 2
0.6186	Remote Similarity	NPD6614	Approved
0.6182	Remote Similarity	NPD6079	Approved
0.6168	Remote Similarity	NPD5786	Approved
0.6154	Remote Similarity	NPD6033	Approved
0.6134	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD5128	Approved
0.6134	Remote Similarity	NPD4730	Approved
0.6134	Remote Similarity	NPD4729	Approved
0.6132	Remote Similarity	NPD4786	Approved
0.6132	Remote Similarity	NPD4197	Approved
0.6094	Remote Similarity	NPD7604	Phase 2
0.608	Remote Similarity	NPD7328	Approved
0.608	Remote Similarity	NPD7327	Approved
0.6078	Remote Similarity	NPD4756	Discovery
0.6075	Remote Similarity	NPD1696	Phase 3
0.6075	Remote Similarity	NPD5329	Approved
0.6075	Remote Similarity	NPD5363	Approved
0.6068	Remote Similarity	NPD6052	Approved
0.6063	Remote Similarity	NPD8033	Approved
0.6063	Remote Similarity	NPD7503	Approved
0.6058	Remote Similarity	NPD5368	Approved
0.6038	Remote Similarity	NPD7154	Phase 3
0.6033	Remote Similarity	NPD5247	Approved
0.6033	Remote Similarity	NPD5251	Approved
0.6033	Remote Similarity	NPD4634	Approved
0.6033	Remote Similarity	NPD5248	Approved
0.6033	Remote Similarity	NPD5250	Approved
0.6033	Remote Similarity	NPD5249	Phase 3
0.6032	Remote Similarity	NPD7516	Approved
0.6019	Remote Similarity	NPD4519	Discontinued

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