NPASS Compound

Structure

NPC471325 OpenBabel07101718312D 27 28 0 0 1 0 0 0 0 0999 V2000 2.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 2.4240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 -2.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7526 1.2660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6366 2.0444 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 -1.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4198 0.0598 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 -1.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5878 0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5257 -1.6920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0257 1.5580 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0834 -1.5229 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.0834 0.5229 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7231 2.4511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9511 -1.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 -1.8688 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0186 0.8688 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.9511 0.3090 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5257 0.6920 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6185 3.4457 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 -2.8634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8090 -1.5878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0859 1.8634 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 13 1 0 0 0 0 2 13 1 0 0 0 0 3 14 1 0 0 0 0 4 15 1 0 0 0 0 5 16 1 0 0 0 0 6 7 1 0 0 0 0 6 8 1 0 0 0 0 7 14 1 0 0 0 0 8 15 2 0 0 0 0 9 14 1 0 0 0 0 9 18 1 0 0 0 0 10 15 1 0 0 0 0 10 19 1 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 12 17 2 0 0 0 0 16 23 2 0 0 0 0 16 26 1 0 0 0 0 17 22 1 0 0 0 0 18 24 2 0 0 0 0 19 21 1 0 0 0 0 19 26 1 1 0 0 0 20 12 1 1 0 0 0 20 21 1 0 0 0 0 20 27 1 0 0 0 0 21 13 1 1 0 0 0 22 25 2 0 0 0 0 22 27 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.22
Volume:	402.724
LogP:	4.024
LogD:	3.693
LogS:	-4.466
# Rotatable Bonds:	3
TPSA:	76.74
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.585
Synthetic Accessibility Score:	5.445
Fsp3:	0.636
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.715
MDCK Permeability:	2.3251208403962664e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.009
Human Intestinal Absorption (HIA):	0.031
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.016

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.721
Plasma Protein Binding (PPB):	95.25926208496094%
Volume Distribution (VD):	0.438
Pgp-substrate:	4.501302719116211%

ADMET: Metabolism

CYP1A2-inhibitor:	0.037
CYP1A2-substrate:	0.088
CYP2C19-inhibitor:	0.037
CYP2C19-substrate:	0.598
CYP2C9-inhibitor:	0.616
CYP2C9-substrate:	0.96
CYP2D6-inhibitor:	0.011
CYP2D6-substrate:	0.22
CYP3A4-inhibitor:	0.23
CYP3A4-substrate:	0.358

ADMET: Excretion

Clearance (CL):	4.392
Half-life (T1/2):	0.842

ADMET: Toxicity

hERG Blockers:	0.001
Human Hepatotoxicity (H-HT):	0.807
Drug-inuced Liver Injury (DILI):	0.877
AMES Toxicity:	0.009
Rat Oral Acute Toxicity:	0.559
Maximum Recommended Daily Dose:	0.055
Skin Sensitization:	0.288
Carcinogencity:	0.112
Eye Corrosion:	0.004
Eye Irritation:	0.025
Respiratory Toxicity:	0.104

Download Data

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

Natural Product: NPC471325

Natural Product ID:	NPC471325
*Common Name:**	Sarcophytonolide J
IUPAC Name:	[(1R,2R,3R,5E)-5,9-dimethyl-11,14-dioxo-2-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-5,13(16)-dien-3-yl] acetate
Synonyms:
Standard InCHIKey:	QWGSYRKRZRCPAG-AXRWLYBBSA-N
Standard InCHI:	InChI=1S/C22H32O5/c1-13(2)21-19(26-16(5)23)10-15(4)8-6-7-14(3)9-18(24)11-17-12-20(21)27-22(17)25/h8,12-14,19-21H,6-7,9-11H2,1-5H3/b15-8+/t14?,19-,20-,21-/m1/s1
SMILES:	CC1CCC=C(CC(C(C2C=C(CC(=O)C1)C(=O)O2)C(C)C)OC(=O)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2414203
PubChem CID:	23624833
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones

*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
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10923847]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[23859780]
NPO20809	Sarcophyton trocheliophorum	Species	Alcyoniidae	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
IC50	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT178	Individual Protein	Protein-tyrosine phosphatase 1B	Homo sapiens	IC50	>=	20.0	ug.mL-1	PMID[490063]

☑ 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 NPC471325 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	213
0.1-0.2	1279
0.2-0.3	5583
0.3-0.4	13077
0.4-0.5	11896
0.5-0.6	6255
0.6-0.7	3366
0.7-0.8	905
0.8-0.85	86
0.85-0.9	28
0.9-0.95	5
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9733	High Similarity	NPC178277
0.96	High Similarity	NPC128276
0.9467	High Similarity	NPC57744
0.9067	High Similarity	NPC259599
0.9067	High Similarity	NPC294434
0.9067	High Similarity	NPC15499
0.9067	High Similarity	NPC117746
0.8987	High Similarity	NPC42470
0.8947	High Similarity	NPC244166
0.8875	High Similarity	NPC173609
0.8831	High Similarity	NPC123360
0.8816	High Similarity	NPC140287
0.8816	High Similarity	NPC474758
0.8816	High Similarity	NPC476355
0.8765	High Similarity	NPC475947
0.875	High Similarity	NPC25684
0.875	High Similarity	NPC281949
0.875	High Similarity	NPC301477
0.8734	High Similarity	NPC270126
0.8718	High Similarity	NPC97516
0.8675	High Similarity	NPC107787
0.8642	High Similarity	NPC35556
0.8554	High Similarity	NPC78089
0.8553	High Similarity	NPC163003
0.8537	High Similarity	NPC474703
0.8519	High Similarity	NPC141810
0.85	High Similarity	NPC471299
0.8481	Intermediate Similarity	NPC171204
0.8481	Intermediate Similarity	NPC476794
0.8481	Intermediate Similarity	NPC65603
0.8481	Intermediate Similarity	NPC470240
0.8481	Intermediate Similarity	NPC141789
0.8481	Intermediate Similarity	NPC476028
0.8481	Intermediate Similarity	NPC187568
0.8481	Intermediate Similarity	NPC41780
0.8462	Intermediate Similarity	NPC226669
0.8462	Intermediate Similarity	NPC155587
0.8462	Intermediate Similarity	NPC138408
0.8462	Intermediate Similarity	NPC193351
0.8452	Intermediate Similarity	NPC469483
0.8452	Intermediate Similarity	NPC261721
0.8434	Intermediate Similarity	NPC115786
0.8409	Intermediate Similarity	NPC476596
0.8395	Intermediate Similarity	NPC281132
0.8375	Intermediate Similarity	NPC299235
0.8375	Intermediate Similarity	NPC93763
0.8375	Intermediate Similarity	NPC108816
0.8354	Intermediate Similarity	NPC235906
0.8313	Intermediate Similarity	NPC193198
0.8313	Intermediate Similarity	NPC318468
0.8312	Intermediate Similarity	NPC84038
0.8295	Intermediate Similarity	NPC476597
0.8295	Intermediate Similarity	NPC476598
0.8293	Intermediate Similarity	NPC325031
0.8276	Intermediate Similarity	NPC471818
0.8272	Intermediate Similarity	NPC469620
0.8272	Intermediate Similarity	NPC617
0.8272	Intermediate Similarity	NPC469690
0.8272	Intermediate Similarity	NPC63649
0.8272	Intermediate Similarity	NPC264227
0.8272	Intermediate Similarity	NPC472965
0.8267	Intermediate Similarity	NPC472266
0.8256	Intermediate Similarity	NPC469653
0.8256	Intermediate Similarity	NPC469631
0.8256	Intermediate Similarity	NPC475906
0.8256	Intermediate Similarity	NPC469628
0.8256	Intermediate Similarity	NPC471047
0.8235	Intermediate Similarity	NPC279859
0.8235	Intermediate Similarity	NPC475461
0.8235	Intermediate Similarity	NPC305475
0.8235	Intermediate Similarity	NPC284902
0.8235	Intermediate Similarity	NPC38576
0.8228	Intermediate Similarity	NPC329852
0.8214	Intermediate Similarity	NPC96259
0.8214	Intermediate Similarity	NPC476804
0.8214	Intermediate Similarity	NPC149869
0.8214	Intermediate Similarity	NPC141193
0.8205	Intermediate Similarity	NPC474705
0.8205	Intermediate Similarity	NPC295633
0.8205	Intermediate Similarity	NPC58956
0.8205	Intermediate Similarity	NPC269206
0.8182	Intermediate Similarity	NPC469660
0.8171	Intermediate Similarity	NPC69271
0.8171	Intermediate Similarity	NPC223904
0.8171	Intermediate Similarity	NPC74673
0.8171	Intermediate Similarity	NPC302426
0.8158	Intermediate Similarity	NPC218477
0.8158	Intermediate Similarity	NPC470256
0.8148	Intermediate Similarity	NPC471220
0.814	Intermediate Similarity	NPC478144
0.814	Intermediate Similarity	NPC475703
0.8125	Intermediate Similarity	NPC27205
0.8118	Intermediate Similarity	NPC255307
0.8118	Intermediate Similarity	NPC165162
0.8118	Intermediate Similarity	NPC215364
0.8118	Intermediate Similarity	NPC189311
0.8095	Intermediate Similarity	NPC53867
0.8095	Intermediate Similarity	NPC169575
0.8095	Intermediate Similarity	NPC475989
0.8095	Intermediate Similarity	NPC40746
0.8095	Intermediate Similarity	NPC39588
0.809	Intermediate Similarity	NPC469645
0.809	Intermediate Similarity	NPC469692
0.8077	Intermediate Similarity	NPC129665
0.8072	Intermediate Similarity	NPC39411
0.8072	Intermediate Similarity	NPC255580
0.8068	Intermediate Similarity	NPC473448
0.8052	Intermediate Similarity	NPC88877
0.8052	Intermediate Similarity	NPC476591
0.8049	Intermediate Similarity	NPC182550
0.8049	Intermediate Similarity	NPC19841
0.8046	Intermediate Similarity	NPC476805
0.8046	Intermediate Similarity	NPC226863
0.8046	Intermediate Similarity	NPC475902
0.8026	Intermediate Similarity	NPC194871
0.8025	Intermediate Similarity	NPC116177
0.8025	Intermediate Similarity	NPC320630
0.8025	Intermediate Similarity	NPC7563
0.8025	Intermediate Similarity	NPC474760
0.8023	Intermediate Similarity	NPC220478
0.8023	Intermediate Similarity	NPC474045
0.8023	Intermediate Similarity	NPC261253
0.8023	Intermediate Similarity	NPC50637
0.8023	Intermediate Similarity	NPC150755
0.8	Intermediate Similarity	NPC121825
0.8	Intermediate Similarity	NPC159635
0.8	Intermediate Similarity	NPC114979
0.8	Intermediate Similarity	NPC329826
0.8	Intermediate Similarity	NPC30486
0.8	Intermediate Similarity	NPC31086
0.8	Intermediate Similarity	NPC470697
0.8	Intermediate Similarity	NPC191476
0.8	Intermediate Similarity	NPC469414
0.8	Intermediate Similarity	NPC324762
0.8	Intermediate Similarity	NPC82297
0.8	Intermediate Similarity	NPC475100
0.7978	Intermediate Similarity	NPC284185
0.7978	Intermediate Similarity	NPC261607
0.7978	Intermediate Similarity	NPC150978
0.7978	Intermediate Similarity	NPC123177
0.7978	Intermediate Similarity	NPC74103
0.7978	Intermediate Similarity	NPC111114
0.7978	Intermediate Similarity	NPC300312
0.7978	Intermediate Similarity	NPC221282
0.7978	Intermediate Similarity	NPC70595
0.7976	Intermediate Similarity	NPC200513
0.7976	Intermediate Similarity	NPC85772
0.7976	Intermediate Similarity	NPC475690
0.7976	Intermediate Similarity	NPC89555
0.7975	Intermediate Similarity	NPC472956
0.7955	Intermediate Similarity	NPC166919
0.7955	Intermediate Similarity	NPC295312
0.7952	Intermediate Similarity	NPC276356
0.7949	Intermediate Similarity	NPC67183
0.7949	Intermediate Similarity	NPC472955
0.7931	Intermediate Similarity	NPC478145
0.7931	Intermediate Similarity	NPC160138
0.7927	Intermediate Similarity	NPC192006
0.7927	Intermediate Similarity	NPC267231
0.7927	Intermediate Similarity	NPC472960
0.7907	Intermediate Similarity	NPC470755
0.7907	Intermediate Similarity	NPC33570
0.7907	Intermediate Similarity	NPC21471
0.7907	Intermediate Similarity	NPC474547
0.7907	Intermediate Similarity	NPC125290
0.7907	Intermediate Similarity	NPC161957
0.7901	Intermediate Similarity	NPC266159
0.7901	Intermediate Similarity	NPC473223
0.7901	Intermediate Similarity	NPC472967
0.7895	Intermediate Similarity	NPC248125
0.7889	Intermediate Similarity	NPC475657
0.7882	Intermediate Similarity	NPC108045
0.7882	Intermediate Similarity	NPC131669
0.7882	Intermediate Similarity	NPC170377
0.7882	Intermediate Similarity	NPC12283
0.7882	Intermediate Similarity	NPC59097
0.7882	Intermediate Similarity	NPC475622
0.7882	Intermediate Similarity	NPC473390
0.7882	Intermediate Similarity	NPC474193
0.7865	Intermediate Similarity	NPC144133
0.7865	Intermediate Similarity	NPC62815
0.7865	Intermediate Similarity	NPC253144
0.7865	Intermediate Similarity	NPC475748
0.7865	Intermediate Similarity	NPC469368
0.7865	Intermediate Similarity	NPC179394
0.7865	Intermediate Similarity	NPC129419
0.7865	Intermediate Similarity	NPC312042
0.7857	Intermediate Similarity	NPC79277
0.7857	Intermediate Similarity	NPC52861
0.7857	Intermediate Similarity	NPC35089
0.7857	Intermediate Similarity	NPC10276
0.7857	Intermediate Similarity	NPC475481
0.7857	Intermediate Similarity	NPC24417
0.7848	Intermediate Similarity	NPC186531
0.7841	Intermediate Similarity	NPC476803
0.7831	Intermediate Similarity	NPC470244
0.7831	Intermediate Similarity	NPC167881
0.7831	Intermediate Similarity	NPC98557
0.7831	Intermediate Similarity	NPC470239
0.7826	Intermediate Similarity	NPC172998

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 NPC471325 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	1852
0.2-0.3	3781
0.3-0.4	2183
0.4-0.5	787
0.5-0.6	272
0.6-0.7	63
0.7-0.8	14
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
0.7976	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD5785	Approved
0.7701	Intermediate Similarity	NPD5363	Approved
0.7701	Intermediate Similarity	NPD1694	Approved
0.7558	Intermediate Similarity	NPD5209	Approved
0.7527	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1733	Clinical (unspecified phase)
0.7473	Intermediate Similarity	NPD46	Approved
0.7473	Intermediate Similarity	NPD6698	Approved
0.7471	Intermediate Similarity	NPD7154	Phase 3
0.7416	Intermediate Similarity	NPD5786	Approved
0.7363	Intermediate Similarity	NPD1695	Approved
0.7356	Intermediate Similarity	NPD4270	Approved
0.7356	Intermediate Similarity	NPD4269	Approved
0.7308	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD5362	Discontinued
0.7241	Intermediate Similarity	NPD5369	Approved
0.7159	Intermediate Similarity	NPD6435	Approved
0.7143	Intermediate Similarity	NPD8039	Approved
0.7129	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4252	Approved
0.7126	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.7111	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7093	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7087	Intermediate Similarity	NPD6371	Approved
0.7033	Intermediate Similarity	NPD7521	Approved
0.7033	Intermediate Similarity	NPD7334	Approved
0.7033	Intermediate Similarity	NPD5330	Approved
0.7033	Intermediate Similarity	NPD6409	Approved
0.7033	Intermediate Similarity	NPD7146	Approved
0.7033	Intermediate Similarity	NPD6684	Approved
0.6947	Remote Similarity	NPD6399	Phase 3
0.6939	Remote Similarity	NPD4225	Approved
0.6932	Remote Similarity	NPD4822	Approved
0.6932	Remote Similarity	NPD5368	Approved
0.6932	Remote Similarity	NPD4821	Approved
0.6932	Remote Similarity	NPD4820	Approved
0.6932	Remote Similarity	NPD4819	Approved
0.6915	Remote Similarity	NPD7838	Discovery
0.6897	Remote Similarity	NPD4268	Approved
0.6897	Remote Similarity	NPD4271	Approved
0.6893	Remote Similarity	NPD6686	Approved
0.6882	Remote Similarity	NPD6903	Approved
0.6882	Remote Similarity	NPD5737	Approved
0.6882	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD6672	Approved
0.6875	Remote Similarity	NPD7900	Approved
0.6875	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6771	Remote Similarity	NPD5779	Approved
0.6771	Remote Similarity	NPD5778	Approved
0.6768	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD5332	Approved
0.6703	Remote Similarity	NPD5331	Approved
0.6697	Remote Similarity	NPD7115	Discovery
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD7983	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6667	Remote Similarity	NPD5693	Phase 1
0.6632	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6101	Approved
0.66	Remote Similarity	NPD7638	Approved
0.6596	Remote Similarity	NPD4251	Approved
0.6596	Remote Similarity	NPD4250	Approved
0.6591	Remote Similarity	NPD4756	Discovery
0.6535	Remote Similarity	NPD7640	Approved
0.6535	Remote Similarity	NPD7639	Approved
0.6531	Remote Similarity	NPD7748	Approved
0.6531	Remote Similarity	NPD5282	Discontinued
0.65	Remote Similarity	NPD6083	Phase 2
0.65	Remote Similarity	NPD6084	Phase 2
0.6495	Remote Similarity	NPD6411	Approved
0.6489	Remote Similarity	NPD4249	Approved
0.6481	Remote Similarity	NPD6053	Discontinued
0.6476	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6465	Remote Similarity	NPD5695	Phase 3
0.6465	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD6673	Approved
0.6458	Remote Similarity	NPD6080	Approved
0.6458	Remote Similarity	NPD6904	Approved
0.6458	Remote Similarity	NPD5370	Suspended
0.6436	Remote Similarity	NPD5696	Approved
0.64	Remote Similarity	NPD7839	Suspended
0.6389	Remote Similarity	NPD6650	Approved
0.6389	Remote Similarity	NPD6649	Approved
0.6386	Remote Similarity	NPD7331	Phase 2
0.6386	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6373	Remote Similarity	NPD6648	Approved
0.6355	Remote Similarity	NPD6372	Approved
0.6355	Remote Similarity	NPD6373	Approved
0.6327	Remote Similarity	NPD6050	Approved
0.6327	Remote Similarity	NPD7637	Suspended
0.6327	Remote Similarity	NPD7515	Phase 2
0.6327	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD6422	Discontinued
0.6311	Remote Similarity	NPD5344	Discontinued
0.6296	Remote Similarity	NPD2067	Discontinued
0.6296	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6289	Remote Similarity	NPD6051	Approved
0.6267	Remote Similarity	NPD6927	Phase 3
0.6262	Remote Similarity	NPD6899	Approved
0.6262	Remote Similarity	NPD6881	Approved
0.625	Remote Similarity	NPD3573	Approved
0.6239	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6226	Remote Similarity	NPD6675	Approved
0.6226	Remote Similarity	NPD6008	Approved
0.6226	Remote Similarity	NPD5739	Approved
0.6226	Remote Similarity	NPD6402	Approved
0.6226	Remote Similarity	NPD7128	Approved
0.6224	Remote Similarity	NPD5207	Approved
0.6224	Remote Similarity	NPD5692	Phase 3
0.6196	Remote Similarity	NPD4695	Discontinued
0.619	Remote Similarity	NPD6647	Phase 2
0.6186	Remote Similarity	NPD5208	Approved
0.6168	Remote Similarity	NPD5697	Approved
0.6162	Remote Similarity	NPD5694	Approved
0.6147	Remote Similarity	NPD6883	Approved
0.6147	Remote Similarity	NPD7102	Approved
0.6147	Remote Similarity	NPD7290	Approved
0.6146	Remote Similarity	NPD6098	Approved
0.6146	Remote Similarity	NPD3618	Phase 1
0.6145	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6111	Remote Similarity	NPD7320	Approved
0.6105	Remote Similarity	NPD3133	Approved
0.6105	Remote Similarity	NPD3666	Approved
0.6105	Remote Similarity	NPD4786	Approved
0.6105	Remote Similarity	NPD3668	Phase 3
0.6105	Remote Similarity	NPD3665	Phase 1
0.6091	Remote Similarity	NPD8130	Phase 1
0.6091	Remote Similarity	NPD6617	Approved
0.6091	Remote Similarity	NPD6847	Approved
0.6091	Remote Similarity	NPD6869	Approved
0.6071	Remote Similarity	NPD7341	Phase 2
0.6064	Remote Similarity	NPD3667	Approved
0.6055	Remote Similarity	NPD6013	Approved
0.6055	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6055	Remote Similarity	NPD6014	Approved
0.6055	Remote Similarity	NPD6012	Approved
0.6055	Remote Similarity	NPD2182	Approved
0.6053	Remote Similarity	NPD29	Approved
0.6053	Remote Similarity	NPD28	Approved
0.604	Remote Similarity	NPD6001	Approved
0.6036	Remote Similarity	NPD6882	Approved
0.6036	Remote Similarity	NPD8297	Approved
0.6024	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6019	Remote Similarity	NPD5701	Approved
0.6	Remote Similarity	NPD5284	Approved
0.6	Remote Similarity	NPD6079	Approved
0.6	Remote Similarity	NPD6110	Phase 1
0.6	Remote Similarity	NPD8034	Phase 2
0.6	Remote Similarity	NPD8035	Phase 2
0.6	Remote Similarity	NPD5281	Approved
0.598	Remote Similarity	NPD4629	Approved
0.598	Remote Similarity	NPD5210	Approved
0.5979	Remote Similarity	NPD5279	Phase 3
0.5963	Remote Similarity	NPD6011	Approved
0.596	Remote Similarity	NPD4753	Phase 2
0.596	Remote Similarity	NPD5328	Approved
0.596	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.5952	Remote Similarity	NPD3197	Phase 1
0.5946	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD7632	Discontinued
0.5922	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.5922	Remote Similarity	NPD4697	Phase 3
0.5922	Remote Similarity	NPD7732	Phase 3
0.5909	Remote Similarity	NPD4691	Approved
0.5897	Remote Similarity	NPD8513	Phase 3
0.5897	Remote Similarity	NPD8516	Approved
0.5897	Remote Similarity	NPD8515	Approved
0.5897	Remote Similarity	NPD8517	Approved
0.5888	Remote Similarity	NPD6052	Approved
0.5872	Remote Similarity	NPD6412	Phase 2
0.5872	Remote Similarity	NPD6614	Approved
0.5854	Remote Similarity	NPD7260	Phase 2
0.5851	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5833	Remote Similarity	NPD7507	Approved
0.5825	Remote Similarity	NPD5654	Approved
0.5823	Remote Similarity	NPD3196	Approved
0.5823	Remote Similarity	NPD3194	Approved
0.5823	Remote Similarity	NPD9298	Approved
0.5823	Remote Similarity	NPD3195	Phase 2
0.5823	Remote Similarity	NPD4266	Approved
0.5816	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.5816	Remote Similarity	NPD4519	Discontinued
0.5816	Remote Similarity	NPD4623	Approved
0.5814	Remote Similarity	NPD3704	Approved
0.5804	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.5798	Remote Similarity	NPD7642	Approved
0.5795	Remote Similarity	NPD4137	Phase 3
0.5794	Remote Similarity	NPD5211	Phase 2
0.5783	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5776	Remote Similarity	NPD7641	Discontinued
0.5769	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5221	Approved
0.5769	Remote Similarity	NPD5222	Approved
0.5766	Remote Similarity	NPD6413	Approved
0.5755	Remote Similarity	NPD4696	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