NPASS Compound

Structure

CID227865 OpenBabel06191716022D 35 39 0 0 1 0 0 0 0 0999 V2000 -3.8234 -3.8430 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2564 0.7044 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7118 -0.0444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7368 0.1781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4538 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 0.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1835 -2.1488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -2.8019 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8745 -1.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 -3.0245 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 1.0827 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 -0.2079 0.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 -2.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6479 0.1235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5144 -2.8920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5873 -0.0388 0.0000 C 0 0 1 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 2.6228 -1.9010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 0.1691 0.0000 C 0 0 2 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 2.6228 -0.0990 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.8963 -0.9898 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8134 -2.4010 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0567 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5362 -2.6840 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0316 -0.7775 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 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 3.2463 0.6828 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7144 -2.8349 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8671 -3.4272 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.2272 -1.7330 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8134 -1.4010 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 28 1 0 0 0 0 4 28 1 0 0 0 0 5 29 1 0 0 0 0 7 9 1 0 0 0 0 7 17 2 0 0 0 0 8 10 2 0 0 0 0 8 20 1 0 0 0 0 9 24 1 0 0 0 0 10 25 1 0 0 0 0 11 13 1 0 0 0 0 11 19 1 0 0 0 0 12 14 1 0 0 0 0 12 21 1 0 0 0 0 13 29 1 0 0 0 0 14 30 1 0 0 0 0 15 19 1 0 0 0 0 15 20 2 0 0 0 0 16 22 1 0 0 0 0 16 23 1 0 0 0 0 17 27 1 0 0 0 0 18 2 1 1 0 0 0 18 21 1 0 0 0 0 19 22 2 0 0 0 0 21 29 1 1 0 0 0 22 30 1 0 0 0 0 23 26 1 0 0 0 0 23 31 1 1 0 0 0 24 18 1 1 0 0 0 24 34 1 0 0 0 0 25 32 2 0 0 0 0 25 35 1 0 0 0 0 26 20 1 1 0 0 0 26 28 1 0 0 0 0 27 33 2 0 0 0 0 27 34 1 0 0 0 0 28 35 1 0 0 0 0 29 30 1 1 0 0 0 30 6 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	480.29
Volume:	512.786
LogP:	5.894
LogD:	4.219
LogS:	-5.14
# Rotatable Bonds:	2
TPSA:	72.83
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.521
Synthetic Accessibility Score:	5.369
Fsp3:	0.667
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.953
MDCK Permeability:	2.614056757010985e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.034
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.999
30% Bioavailability (F30%):	0.953

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.013
Plasma Protein Binding (PPB):	98.22232818603516%
Volume Distribution (VD):	2.734
Pgp-substrate:	3.6733920574188232%

ADMET: Metabolism

CYP1A2-inhibitor:	0.032
CYP1A2-substrate:	0.169
CYP2C19-inhibitor:	0.78
CYP2C19-substrate:	0.902
CYP2C9-inhibitor:	0.888
CYP2C9-substrate:	0.209
CYP2D6-inhibitor:	0.56
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.927
CYP3A4-substrate:	0.813

ADMET: Excretion

Clearance (CL):	3.689
Half-life (T1/2):	0.189

ADMET: Toxicity

hERG Blockers:	0.446
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.102
AMES Toxicity:	0.016
Rat Oral Acute Toxicity:	0.7
Maximum Recommended Daily Dose:	0.962
Skin Sensitization:	0.963
Carcinogencity:	0.675
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.964

Download Data

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

Natural Product: NPC227865

Natural Product ID:	NPC227865
*Common Name:**	Lancilactone A
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	XOZSMWFUVBFKTJ-BCXZRNOBSA-N
Standard InCHI:	InChI=1S/C30H40O5/c1-17-7-9-24(34-27(17)33)18(2)21-12-14-30(6)22-16-23(31)26-20(8-10-25(32)35-28(26,3)4)15-19(22)11-13-29(21,30)5/h7-8,10,15,18,21,23-24,26,31H,9,11-14,16H2,1-6H3/t18-,21+,23+,24-,26-,29+,30-/m0/s1
SMILES:	CC1=CC[C@@H]([C@@H](C)[C@H]2CC[C@@]3(C)C4=C(CC[C@]23C)C=C2C=CC(=O)OC(C)(C)[C@@H]2[C@@H](C4)O)OC1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL451975
PubChem CID:	10719539
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
NPO19455	Kadsura lancilimba	Species	Schisandraceae	Eukaryota	n.a.	stem	n.a.	PMID[9917290]
NPO19455	Kadsura lancilimba	Species	Schisandraceae	Eukaryota	n.a.	root	n.a.	PMID[9917290]
NPO19455	Kadsura lancilimba	Species	Schisandraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT759	Cell Line	H9	Homo sapiens	IC50	=	14.3	ug.mL-1	PMID[461088]

☑ 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 NPC227865 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	189
0.1-0.2	998
0.2-0.3	4279
0.3-0.4	12671
0.4-0.5	11685
0.5-0.6	7564
0.6-0.7	4605
0.7-0.8	657
0.8-0.85	21
0.85-0.9	13
0.9-0.95	12
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9479	High Similarity	NPC183570
0.9457	High Similarity	NPC120351
0.9457	High Similarity	NPC471994
0.9457	High Similarity	NPC166143
0.9368	High Similarity	NPC290802
0.9278	High Similarity	NPC280566
0.9184	High Similarity	NPC272632
0.9158	High Similarity	NPC202705
0.8922	High Similarity	NPC181298
0.8878	High Similarity	NPC298233
0.8835	High Similarity	NPC255401
0.8835	High Similarity	NPC284162
0.8824	High Similarity	NPC475274
0.8738	High Similarity	NPC238850
0.87	High Similarity	NPC297617
0.8654	High Similarity	NPC262083
0.8654	High Similarity	NPC71680
0.8654	High Similarity	NPC471484
0.86	High Similarity	NPC471993
0.8558	High Similarity	NPC15551
0.8396	Intermediate Similarity	NPC241477
0.8365	Intermediate Similarity	NPC220155
0.8229	Intermediate Similarity	NPC177141
0.82	Intermediate Similarity	NPC141401
0.8163	Intermediate Similarity	NPC162615
0.8163	Intermediate Similarity	NPC152778
0.8163	Intermediate Similarity	NPC205034
0.8144	Intermediate Similarity	NPC273199
0.8131	Intermediate Similarity	NPC474315
0.8131	Intermediate Similarity	NPC470076
0.8119	Intermediate Similarity	NPC92275
0.8119	Intermediate Similarity	NPC98868
0.8113	Intermediate Similarity	NPC75389
0.8113	Intermediate Similarity	NPC137911
0.8113	Intermediate Similarity	NPC228477
0.81	Intermediate Similarity	NPC16967
0.81	Intermediate Similarity	NPC190713
0.8095	Intermediate Similarity	NPC91034
0.8073	Intermediate Similarity	NPC216665
0.8058	Intermediate Similarity	NPC155332
0.8058	Intermediate Similarity	NPC32577
0.8058	Intermediate Similarity	NPC114540
0.8058	Intermediate Similarity	NPC475320
0.802	Intermediate Similarity	NPC99726
0.8019	Intermediate Similarity	NPC275060
0.8	Intermediate Similarity	NPC266570
0.8	Intermediate Similarity	NPC281134
0.8	Intermediate Similarity	NPC171395
0.7981	Intermediate Similarity	NPC171014
0.798	Intermediate Similarity	NPC214697
0.7979	Intermediate Similarity	NPC474809
0.7959	Intermediate Similarity	NPC310479
0.7959	Intermediate Similarity	NPC182136
0.7941	Intermediate Similarity	NPC57079
0.7941	Intermediate Similarity	NPC108368
0.7928	Intermediate Similarity	NPC476959
0.7925	Intermediate Similarity	NPC43063
0.7925	Intermediate Similarity	NPC476958
0.7925	Intermediate Similarity	NPC475294
0.7925	Intermediate Similarity	NPC79298
0.7909	Intermediate Similarity	NPC43213
0.7905	Intermediate Similarity	NPC309190
0.79	Intermediate Similarity	NPC191521
0.79	Intermediate Similarity	NPC104925
0.79	Intermediate Similarity	NPC469491
0.79	Intermediate Similarity	NPC298973
0.789	Intermediate Similarity	NPC191620
0.789	Intermediate Similarity	NPC44537
0.7879	Intermediate Similarity	NPC234335
0.7879	Intermediate Similarity	NPC177641
0.7879	Intermediate Similarity	NPC212948
0.787	Intermediate Similarity	NPC29133
0.787	Intermediate Similarity	NPC37116
0.7857	Intermediate Similarity	NPC146554
0.785	Intermediate Similarity	NPC304276
0.785	Intermediate Similarity	NPC137462
0.7838	Intermediate Similarity	NPC470075
0.783	Intermediate Similarity	NPC189863
0.783	Intermediate Similarity	NPC295843
0.7822	Intermediate Similarity	NPC33473
0.7818	Intermediate Similarity	NPC122056
0.7812	Intermediate Similarity	NPC471795
0.781	Intermediate Similarity	NPC112009
0.781	Intermediate Similarity	NPC23584
0.78	Intermediate Similarity	NPC472954
0.78	Intermediate Similarity	NPC38232
0.7798	Intermediate Similarity	NPC470961
0.7789	Intermediate Similarity	NPC23748
0.7788	Intermediate Similarity	NPC99411
0.7788	Intermediate Similarity	NPC146822
0.7788	Intermediate Similarity	NPC244456
0.7788	Intermediate Similarity	NPC469657
0.7788	Intermediate Similarity	NPC115899
0.7778	Intermediate Similarity	NPC221111
0.7778	Intermediate Similarity	NPC280149
0.7778	Intermediate Similarity	NPC475065
0.7778	Intermediate Similarity	NPC78973
0.7767	Intermediate Similarity	NPC474440
0.7767	Intermediate Similarity	NPC65700
0.7767	Intermediate Similarity	NPC218107
0.7767	Intermediate Similarity	NPC235464
0.7767	Intermediate Similarity	NPC181147
0.7767	Intermediate Similarity	NPC166745
0.7757	Intermediate Similarity	NPC329048
0.7757	Intermediate Similarity	NPC330011
0.7748	Intermediate Similarity	NPC67259
0.7748	Intermediate Similarity	NPC147912
0.7745	Intermediate Similarity	NPC473153
0.7736	Intermediate Similarity	NPC472822
0.7727	Intermediate Similarity	NPC221144
0.7727	Intermediate Similarity	NPC236217
0.7727	Intermediate Similarity	NPC475524
0.7727	Intermediate Similarity	NPC100267
0.7723	Intermediate Similarity	NPC279410
0.7723	Intermediate Similarity	NPC119562
0.7723	Intermediate Similarity	NPC201725
0.7723	Intermediate Similarity	NPC469697
0.7714	Intermediate Similarity	NPC11956
0.7706	Intermediate Similarity	NPC16270
0.7706	Intermediate Similarity	NPC473627
0.7706	Intermediate Similarity	NPC103491
0.7706	Intermediate Similarity	NPC12795
0.77	Intermediate Similarity	NPC72845
0.77	Intermediate Similarity	NPC303697
0.7692	Intermediate Similarity	NPC241221
0.7692	Intermediate Similarity	NPC476299
0.7692	Intermediate Similarity	NPC266955
0.7692	Intermediate Similarity	NPC474012
0.7692	Intermediate Similarity	NPC473510
0.7685	Intermediate Similarity	NPC318363
0.7685	Intermediate Similarity	NPC475418
0.7685	Intermediate Similarity	NPC473482
0.7677	Intermediate Similarity	NPC210216
0.7677	Intermediate Similarity	NPC5509
0.7677	Intermediate Similarity	NPC470734
0.7677	Intermediate Similarity	NPC472240
0.7677	Intermediate Similarity	NPC262858
0.7677	Intermediate Similarity	NPC174342
0.767	Intermediate Similarity	NPC210337
0.767	Intermediate Similarity	NPC208094
0.767	Intermediate Similarity	NPC110937
0.7664	Intermediate Similarity	NPC93026
0.7664	Intermediate Similarity	NPC265502
0.7664	Intermediate Similarity	NPC29389
0.7664	Intermediate Similarity	NPC469960
0.7664	Intermediate Similarity	NPC477125
0.7658	Intermediate Similarity	NPC241977
0.7658	Intermediate Similarity	NPC171126
0.7653	Intermediate Similarity	NPC149224
0.7653	Intermediate Similarity	NPC312561
0.7653	Intermediate Similarity	NPC199382
0.7647	Intermediate Similarity	NPC474909
0.7647	Intermediate Similarity	NPC20546
0.7647	Intermediate Similarity	NPC276110
0.7647	Intermediate Similarity	NPC293052
0.7647	Intermediate Similarity	NPC295347
0.7647	Intermediate Similarity	NPC209355
0.7642	Intermediate Similarity	NPC180204
0.7642	Intermediate Similarity	NPC473283
0.7642	Intermediate Similarity	NPC329345
0.7642	Intermediate Similarity	NPC85742
0.7642	Intermediate Similarity	NPC475526
0.7642	Intermediate Similarity	NPC72151
0.7629	Intermediate Similarity	NPC109528
0.7624	Intermediate Similarity	NPC115021
0.7619	Intermediate Similarity	NPC282524
0.7619	Intermediate Similarity	NPC476240
0.7619	Intermediate Similarity	NPC476223
0.7619	Intermediate Similarity	NPC224720
0.7619	Intermediate Similarity	NPC310981
0.7611	Intermediate Similarity	NPC185287
0.7611	Intermediate Similarity	NPC167606
0.7611	Intermediate Similarity	NPC157380
0.7611	Intermediate Similarity	NPC286528
0.7611	Intermediate Similarity	NPC20302
0.7611	Intermediate Similarity	NPC140055
0.7609	Intermediate Similarity	NPC476317
0.7604	Intermediate Similarity	NPC311070
0.7604	Intermediate Similarity	NPC472377
0.7604	Intermediate Similarity	NPC49208
0.7604	Intermediate Similarity	NPC474193
0.7604	Intermediate Similarity	NPC42476
0.7604	Intermediate Similarity	NPC12283
0.76	Intermediate Similarity	NPC212679
0.76	Intermediate Similarity	NPC469372
0.76	Intermediate Similarity	NPC469595
0.76	Intermediate Similarity	NPC477147
0.76	Intermediate Similarity	NPC220454
0.76	Intermediate Similarity	NPC281942
0.76	Intermediate Similarity	NPC477149
0.76	Intermediate Similarity	NPC232426
0.7596	Intermediate Similarity	NPC278673
0.7596	Intermediate Similarity	NPC64742
0.7593	Intermediate Similarity	NPC472263
0.7593	Intermediate Similarity	NPC109376
0.7593	Intermediate Similarity	NPC469957
0.7593	Intermediate Similarity	NPC473284
0.7593	Intermediate Similarity	NPC469959
0.7593	Intermediate Similarity	NPC108682
0.7589	Intermediate Similarity	NPC82759

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 NPC227865 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	158
0.1-0.2	1277
0.2-0.3	3812
0.3-0.4	2692
0.4-0.5	779
0.5-0.6	241
0.6-0.7	185
0.7-0.8	6
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
0.7611	Intermediate Similarity	NPD7115	Discovery
0.7525	Intermediate Similarity	NPD7637	Suspended
0.7429	Intermediate Similarity	NPD7638	Approved
0.7411	Intermediate Similarity	NPD6053	Discontinued
0.7358	Intermediate Similarity	NPD7640	Approved
0.7358	Intermediate Similarity	NPD7639	Approved
0.735	Intermediate Similarity	NPD7503	Approved
0.7347	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD6084	Phase 2
0.7333	Intermediate Similarity	NPD6083	Phase 2
0.7327	Intermediate Similarity	NPD6051	Approved
0.7264	Intermediate Similarity	NPD4225	Approved
0.7245	Intermediate Similarity	NPD6695	Phase 3
0.7207	Intermediate Similarity	NPD6881	Approved
0.7207	Intermediate Similarity	NPD6899	Approved
0.7172	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5695	Phase 3
0.7117	Intermediate Similarity	NPD5697	Approved
0.7115	Intermediate Similarity	NPD6399	Phase 3
0.7087	Intermediate Similarity	NPD7838	Discovery
0.7087	Intermediate Similarity	NPD5785	Approved
0.708	Intermediate Similarity	NPD7102	Approved
0.708	Intermediate Similarity	NPD7290	Approved
0.708	Intermediate Similarity	NPD6883	Approved
0.7027	Intermediate Similarity	NPD7128	Approved
0.7027	Intermediate Similarity	NPD5739	Approved
0.7027	Intermediate Similarity	NPD6675	Approved
0.7027	Intermediate Similarity	NPD6402	Approved
0.7021	Intermediate Similarity	NPD6924	Approved
0.7021	Intermediate Similarity	NPD6926	Approved
0.7019	Intermediate Similarity	NPD5281	Approved
0.7019	Intermediate Similarity	NPD5284	Approved
0.7019	Intermediate Similarity	NPD6411	Approved
0.7018	Intermediate Similarity	NPD8130	Phase 1
0.7018	Intermediate Similarity	NPD6847	Approved
0.7018	Intermediate Similarity	NPD6649	Approved
0.7018	Intermediate Similarity	NPD6617	Approved
0.7018	Intermediate Similarity	NPD6650	Approved
0.7018	Intermediate Similarity	NPD6869	Approved
0.6991	Remote Similarity	NPD6013	Approved
0.6991	Remote Similarity	NPD6014	Approved
0.6991	Remote Similarity	NPD6012	Approved
0.697	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6961	Remote Similarity	NPD7750	Discontinued
0.6961	Remote Similarity	NPD7524	Approved
0.6957	Remote Similarity	NPD8297	Approved
0.6957	Remote Similarity	NPD6882	Approved
0.6952	Remote Similarity	NPD5779	Approved
0.6952	Remote Similarity	NPD5778	Approved
0.6944	Remote Similarity	NPD5696	Approved
0.6939	Remote Similarity	NPD6930	Phase 2
0.6939	Remote Similarity	NPD7514	Phase 3
0.6939	Remote Similarity	NPD6931	Approved
0.693	Remote Similarity	NPD6371	Approved
0.6903	Remote Similarity	NPD6011	Approved
0.6903	Remote Similarity	NPD7320	Approved
0.6893	Remote Similarity	NPD6672	Approved
0.6893	Remote Similarity	NPD5737	Approved
0.6875	Remote Similarity	NPD6933	Approved
0.6863	Remote Similarity	NPD5279	Phase 3
0.6863	Remote Similarity	NPD7146	Approved
0.6863	Remote Similarity	NPD6684	Approved
0.6863	Remote Similarity	NPD7334	Approved
0.6863	Remote Similarity	NPD6409	Approved
0.6863	Remote Similarity	NPD5330	Approved
0.6863	Remote Similarity	NPD7521	Approved
0.6857	Remote Similarity	NPD5694	Approved
0.6857	Remote Similarity	NPD5693	Phase 1
0.6857	Remote Similarity	NPD6079	Approved
0.6857	Remote Similarity	NPD6050	Approved
0.6842	Remote Similarity	NPD6372	Approved
0.6842	Remote Similarity	NPD6373	Approved
0.6837	Remote Similarity	NPD6929	Approved
0.6837	Remote Similarity	NPD4195	Approved
0.6832	Remote Similarity	NPD4786	Approved
0.6827	Remote Similarity	NPD6101	Approved
0.6827	Remote Similarity	NPD4753	Phase 2
0.6827	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5210	Approved
0.6822	Remote Similarity	NPD4629	Approved
0.6822	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD5701	Approved
0.6804	Remote Similarity	NPD6932	Approved
0.6789	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD6942	Approved
0.6771	Remote Similarity	NPD7339	Approved
0.6768	Remote Similarity	NPD7332	Phase 2
0.6768	Remote Similarity	NPD4820	Approved
0.6768	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD4821	Approved
0.6768	Remote Similarity	NPD4822	Approved
0.6768	Remote Similarity	NPD4819	Approved
0.6765	Remote Similarity	NPD1694	Approved
0.6765	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5692	Phase 3
0.6762	Remote Similarity	NPD5207	Approved
0.6757	Remote Similarity	NPD5211	Phase 2
0.6757	Remote Similarity	NPD7632	Discontinued
0.6754	Remote Similarity	NPD6686	Approved
0.6735	Remote Similarity	NPD7145	Approved
0.6735	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD5362	Discontinued
0.6731	Remote Similarity	NPD6903	Approved
0.6731	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5286	Approved
0.6727	Remote Similarity	NPD4696	Approved
0.6727	Remote Similarity	NPD6648	Approved
0.6727	Remote Similarity	NPD5285	Approved
0.6702	Remote Similarity	NPD7144	Approved
0.6702	Remote Similarity	NPD7143	Approved
0.67	Remote Similarity	NPD6902	Approved
0.6698	Remote Similarity	NPD7087	Discontinued
0.6667	Remote Similarity	NPD3133	Approved
0.6667	Remote Similarity	NPD5328	Approved
0.6667	Remote Similarity	NPD7327	Approved
0.6667	Remote Similarity	NPD5344	Discontinued
0.6667	Remote Similarity	NPD6904	Approved
0.6667	Remote Similarity	NPD6080	Approved
0.6667	Remote Similarity	NPD3666	Approved
0.6667	Remote Similarity	NPD3665	Phase 1
0.6667	Remote Similarity	NPD7328	Approved
0.6667	Remote Similarity	NPD6673	Approved
0.6639	Remote Similarity	NPD8033	Approved
0.6637	Remote Similarity	NPD5141	Approved
0.6634	Remote Similarity	NPD3667	Approved
0.6634	Remote Similarity	NPD5209	Approved
0.6633	Remote Similarity	NPD6925	Approved
0.6633	Remote Similarity	NPD5776	Phase 2
0.6632	Remote Similarity	NPD7150	Approved
0.6632	Remote Similarity	NPD7152	Approved
0.6632	Remote Similarity	NPD7151	Approved
0.6612	Remote Similarity	NPD7516	Approved
0.6612	Remote Similarity	NPD7100	Approved
0.6612	Remote Similarity	NPD7101	Approved
0.6607	Remote Similarity	NPD5225	Approved
0.6607	Remote Similarity	NPD5224	Approved
0.6607	Remote Similarity	NPD5226	Approved
0.6607	Remote Similarity	NPD4633	Approved
0.6606	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5222	Approved
0.6606	Remote Similarity	NPD5221	Approved
0.6602	Remote Similarity	NPD5363	Approved
0.6602	Remote Similarity	NPD6893	Approved
0.66	Remote Similarity	NPD7525	Registered
0.6598	Remote Similarity	NPD8039	Approved
0.6598	Remote Similarity	NPD8264	Approved
0.6596	Remote Similarity	NPD6923	Approved
0.6596	Remote Similarity	NPD6922	Approved
0.6581	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD6404	Discontinued
0.6574	Remote Similarity	NPD7748	Approved
0.6569	Remote Similarity	NPD5332	Approved
0.6569	Remote Similarity	NPD7154	Phase 3
0.6569	Remote Similarity	NPD5331	Approved
0.6566	Remote Similarity	NPD4271	Approved
0.6566	Remote Similarity	NPD4268	Approved
0.6557	Remote Similarity	NPD8294	Approved
0.6557	Remote Similarity	NPD8377	Approved
0.6549	Remote Similarity	NPD5174	Approved
0.6549	Remote Similarity	NPD5175	Approved
0.6545	Remote Similarity	NPD5173	Approved
0.6545	Remote Similarity	NPD4755	Approved
0.6542	Remote Similarity	NPD7515	Phase 2
0.6538	Remote Similarity	NPD5280	Approved
0.6538	Remote Similarity	NPD5690	Phase 2
0.6538	Remote Similarity	NPD4694	Approved
0.6538	Remote Similarity	NPD3618	Phase 1
0.6535	Remote Similarity	NPD4790	Discontinued
0.6531	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD6335	Approved
0.6518	Remote Similarity	NPD5223	Approved
0.6514	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD8296	Approved
0.6504	Remote Similarity	NPD8378	Approved
0.6504	Remote Similarity	NPD8380	Approved
0.6504	Remote Similarity	NPD8335	Approved
0.6504	Remote Similarity	NPD8379	Approved
0.65	Remote Similarity	NPD6683	Phase 2
0.65	Remote Similarity	NPD6274	Approved
0.65	Remote Similarity	NPD6868	Approved
0.6495	Remote Similarity	NPD4785	Approved
0.6495	Remote Similarity	NPD4784	Approved
0.6481	Remote Similarity	NPD4202	Approved
0.6476	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4632	Approved
0.6471	Remote Similarity	NPD4221	Approved
0.6471	Remote Similarity	NPD4223	Phase 3
0.6449	Remote Similarity	NPD46	Approved
0.6449	Remote Similarity	NPD6698	Approved
0.6446	Remote Similarity	NPD6317	Approved
0.6442	Remote Similarity	NPD1696	Phase 3
0.6442	Remote Similarity	NPD5329	Approved
0.6436	Remote Similarity	NPD7509	Discontinued
0.6434	Remote Similarity	NPD7260	Phase 2
0.6429	Remote Similarity	NPD7507	Approved
0.6429	Remote Similarity	NPD4700	Approved
0.6423	Remote Similarity	NPD6319	Approved
0.6415	Remote Similarity	NPD4518	Approved
0.6415	Remote Similarity	NPD5208	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