NPASS Compound

Structure

NPC294434 OpenBabel07101719132D 24 25 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 -1.5388 -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 0.5257 -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 -0.0186 0.8688 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 0 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 0.9511 -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 0.5257 0.6920 0.0000 C 0 0 2 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 0.9511 0.3090 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 0.0859 -2.8634 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8968 1.7601 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 3 13 1 0 0 0 0 4 14 1 0 0 0 0 5 6 1 0 0 0 0 5 7 1 0 0 0 0 6 13 1 0 0 0 0 7 14 2 0 0 0 0 8 13 2 0 0 0 0 8 16 1 0 0 0 0 9 15 1 0 0 0 0 9 16 1 0 0 0 0 10 15 2 0 0 0 0 11 17 1 0 0 0 0 11 18 1 0 0 0 0 14 18 1 0 0 0 0 15 20 1 0 0 0 0 16 21 2 0 0 0 0 17 12 1 6 0 0 0 17 19 1 0 0 0 0 18 22 2 0 0 0 0 19 10 1 1 0 0 0 19 24 1 0 0 0 0 20 23 2 0 0 0 0 20 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	330.18
Volume:	356.705
LogP:	3.391
LogD:	2.368
LogS:	-3.382
# Rotatable Bonds:	0
TPSA:	67.51
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.713
Synthetic Accessibility Score:	5.539
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.644
MDCK Permeability:	1.647634053369984e-05
Pgp-inhibitor:	0.024
Pgp-substrate:	0.522
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.001

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.141
Plasma Protein Binding (PPB):	92.95690155029297%
Volume Distribution (VD):	1.396
Pgp-substrate:	11.772068977355957%

ADMET: Metabolism

CYP1A2-inhibitor:	0.212
CYP1A2-substrate:	0.337
CYP2C19-inhibitor:	0.112
CYP2C19-substrate:	0.333
CYP2C9-inhibitor:	0.679
CYP2C9-substrate:	0.882
CYP2D6-inhibitor:	0.036
CYP2D6-substrate:	0.387
CYP3A4-inhibitor:	0.203
CYP3A4-substrate:	0.311

ADMET: Excretion

Clearance (CL):	13.761
Half-life (T1/2):	0.927

ADMET: Toxicity

hERG Blockers:	0.003
Human Hepatotoxicity (H-HT):	0.129
Drug-inuced Liver Injury (DILI):	0.933
AMES Toxicity:	0.02
Rat Oral Acute Toxicity:	0.826
Maximum Recommended Daily Dose:	0.04
Skin Sensitization:	0.543
Carcinogencity:	0.823
Eye Corrosion:	0.047
Eye Irritation:	0.038
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: NPC294434

Natural Product ID:	NPC294434
*Common Name:**	Sarcostolide B
IUPAC Name:	(1S,2R,5E,9Z)-5,9-dimethyl-2-propan-2-yl-15-oxabicyclo[11.2.1]hexadeca-5,9,13(16)-triene-4,11,14-trione
Synonyms:
Standard InCHIKey:	SLQVZPZHWRKZDO-BVBPSWRCSA-N
Standard InCHI:	InChI=1S/C20H26O4/c1-12(2)17-11-18(22)14(4)7-5-6-13(3)8-16(21)9-15-10-19(17)24-20(15)23/h7-8,10,12,17,19H,5-6,9,11H2,1-4H3/b13-8-,14-7+/t17-,19-/m1/s1
SMILES:	CC(C)[C@H]1CC(=O)/C(=C/CC/C(=CC(=O)CC2=C[C@H]1OC2=O)/C)/C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL528994
PubChem CID:	24970449
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0001538] Diterpene 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
NPO29001	Sarcophyton stolidotum	Species	Orchidaceae	Eukaryota	n.a.	taiwanese soft coral	n.a.	PMID[18537291]
NPO29001	Sarcophyton stolidotum	Species	Orchidaceae	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	2

Activity Type	# Activity
Cell Line	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT165	Cell Line	HeLa	Homo sapiens	Inhibition	=	5.88	%	PMID[492071]
NPT1183	Cell Line	WiDr	Homo sapiens	Inhibition	=	8.31	%	PMID[492071]

☑ 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 NPC294434 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	191
0.1-0.2	1387
0.2-0.3	6931
0.3-0.4	16781
0.4-0.5	8918
0.5-0.6	5601
0.6-0.7	2402
0.7-0.8	448
0.8-0.85	26
0.85-0.9	2
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC259599
1.0	High Similarity	NPC117746
1.0	High Similarity	NPC15499
0.9577	High Similarity	NPC57744
0.9444	High Similarity	NPC128276
0.9315	High Similarity	NPC178277
0.9155	High Similarity	NPC474758
0.9067	High Similarity	NPC471325
0.9067	High Similarity	NPC42470
0.8767	High Similarity	NPC329852
0.8714	High Similarity	NPC470256
0.8649	High Similarity	NPC123360
0.863	High Similarity	NPC476355
0.8571	High Similarity	NPC194871
0.8514	High Similarity	NPC244166
0.8462	Intermediate Similarity	NPC173609
0.8429	Intermediate Similarity	NPC248125
0.8378	Intermediate Similarity	NPC140287
0.8356	Intermediate Similarity	NPC163003
0.8333	Intermediate Similarity	NPC476591
0.8333	Intermediate Similarity	NPC88877
0.8312	Intermediate Similarity	NPC270126
0.831	Intermediate Similarity	NPC472266
0.8286	Intermediate Similarity	NPC470688
0.8194	Intermediate Similarity	NPC276290
0.8182	Intermediate Similarity	NPC108816
0.8182	Intermediate Similarity	NPC93763
0.8125	Intermediate Similarity	NPC475947
0.8116	Intermediate Similarity	NPC151648
0.8108	Intermediate Similarity	NPC129665
0.8101	Intermediate Similarity	NPC325031
0.8101	Intermediate Similarity	NPC281949
0.8101	Intermediate Similarity	NPC301477
0.8101	Intermediate Similarity	NPC25684
0.8082	Intermediate Similarity	NPC265574
0.8056	Intermediate Similarity	NPC203335
0.8052	Intermediate Similarity	NPC141789
0.8052	Intermediate Similarity	NPC187568
0.8052	Intermediate Similarity	NPC65603
0.8052	Intermediate Similarity	NPC476794
0.8052	Intermediate Similarity	NPC41780
0.8052	Intermediate Similarity	NPC476028
0.8052	Intermediate Similarity	NPC171204
0.8052	Intermediate Similarity	NPC470240
0.8052	Intermediate Similarity	NPC97516
0.8049	Intermediate Similarity	NPC107787
0.8049	Intermediate Similarity	NPC38576
0.8049	Intermediate Similarity	NPC279859
0.8049	Intermediate Similarity	NPC261721
0.8026	Intermediate Similarity	NPC138408
0.8026	Intermediate Similarity	NPC193351
0.8026	Intermediate Similarity	NPC155587
0.8026	Intermediate Similarity	NPC226669
0.8025	Intermediate Similarity	NPC149869
0.8	Intermediate Similarity	NPC474658
0.8	Intermediate Similarity	NPC269206
0.8	Intermediate Similarity	NPC295633
0.8	Intermediate Similarity	NPC35556
0.8	Intermediate Similarity	NPC58956
0.7975	Intermediate Similarity	NPC281132
0.7973	Intermediate Similarity	NPC67183
0.7973	Intermediate Similarity	NPC469660
0.7949	Intermediate Similarity	NPC471220
0.7949	Intermediate Similarity	NPC299235
0.7949	Intermediate Similarity	NPC253749
0.7945	Intermediate Similarity	NPC218477
0.7927	Intermediate Similarity	NPC189311
0.7927	Intermediate Similarity	NPC215364
0.7927	Intermediate Similarity	NPC78089
0.7922	Intermediate Similarity	NPC235906
0.7922	Intermediate Similarity	NPC27205
0.7901	Intermediate Similarity	NPC318468
0.7901	Intermediate Similarity	NPC193198
0.7901	Intermediate Similarity	NPC474703
0.7882	Intermediate Similarity	NPC471818
0.7875	Intermediate Similarity	NPC141810
0.7875	Intermediate Similarity	NPC275507
0.7867	Intermediate Similarity	NPC67076
0.7867	Intermediate Similarity	NPC84038
0.7867	Intermediate Similarity	NPC319163
0.7867	Intermediate Similarity	NPC257618
0.7857	Intermediate Similarity	NPC471047
0.7857	Intermediate Similarity	NPC469631
0.7857	Intermediate Similarity	NPC469628
0.7857	Intermediate Similarity	NPC475906
0.7857	Intermediate Similarity	NPC226863
0.7857	Intermediate Similarity	NPC469653
0.7848	Intermediate Similarity	NPC469620
0.7848	Intermediate Similarity	NPC472965
0.7848	Intermediate Similarity	NPC63649
0.7848	Intermediate Similarity	NPC471299
0.7848	Intermediate Similarity	NPC469690
0.7848	Intermediate Similarity	NPC264227
0.7838	Intermediate Similarity	NPC470693
0.7831	Intermediate Similarity	NPC469483
0.7831	Intermediate Similarity	NPC284902
0.7821	Intermediate Similarity	NPC10572
0.7821	Intermediate Similarity	NPC116177
0.7821	Intermediate Similarity	NPC7563
0.7821	Intermediate Similarity	NPC320630
0.7821	Intermediate Similarity	NPC471225
0.7821	Intermediate Similarity	NPC474760
0.7805	Intermediate Similarity	NPC30486
0.7805	Intermediate Similarity	NPC476804
0.7805	Intermediate Similarity	NPC475100
0.7805	Intermediate Similarity	NPC115786
0.7778	Intermediate Similarity	NPC200513
0.7778	Intermediate Similarity	NPC85772
0.7763	Intermediate Similarity	NPC474705
0.775	Intermediate Similarity	NPC69271
0.775	Intermediate Similarity	NPC74673
0.775	Intermediate Similarity	NPC302426
0.775	Intermediate Similarity	NPC223904
0.7746	Intermediate Similarity	NPC155849
0.7746	Intermediate Similarity	NPC217940
0.7738	Intermediate Similarity	NPC160138
0.7738	Intermediate Similarity	NPC475703
0.7738	Intermediate Similarity	NPC478144
0.7722	Intermediate Similarity	NPC267231
0.7711	Intermediate Similarity	NPC125290
0.7711	Intermediate Similarity	NPC155873
0.7692	Intermediate Similarity	NPC266159
0.7692	Intermediate Similarity	NPC473223
0.7692	Intermediate Similarity	NPC472967
0.7683	Intermediate Similarity	NPC169575
0.7683	Intermediate Similarity	NPC39588
0.7683	Intermediate Similarity	NPC53867
0.7683	Intermediate Similarity	NPC40746
0.7683	Intermediate Similarity	NPC170286
0.7662	Intermediate Similarity	NPC476590
0.7662	Intermediate Similarity	NPC114727
0.7647	Intermediate Similarity	NPC476805
0.7639	Intermediate Similarity	NPC34883
0.7632	Intermediate Similarity	NPC186531
0.7625	Intermediate Similarity	NPC617
0.7625	Intermediate Similarity	NPC182550
0.7619	Intermediate Similarity	NPC261253
0.7619	Intermediate Similarity	NPC474045
0.7619	Intermediate Similarity	NPC475461
0.7619	Intermediate Similarity	NPC305475
0.7614	Intermediate Similarity	NPC476596
0.76	Intermediate Similarity	NPC144511
0.76	Intermediate Similarity	NPC232812
0.76	Intermediate Similarity	NPC296522
0.76	Intermediate Similarity	NPC151481
0.7595	Intermediate Similarity	NPC68156
0.759	Intermediate Similarity	NPC96259
0.759	Intermediate Similarity	NPC38569
0.759	Intermediate Similarity	NPC141193
0.759	Intermediate Similarity	NPC82297
0.759	Intermediate Similarity	NPC163615
0.759	Intermediate Similarity	NPC474359
0.7586	Intermediate Similarity	NPC284185
0.7558	Intermediate Similarity	NPC295312
0.7558	Intermediate Similarity	NPC5509
0.7558	Intermediate Similarity	NPC78008
0.7532	Intermediate Similarity	NPC222244
0.7532	Intermediate Similarity	NPC16349
0.7532	Intermediate Similarity	NPC287878
0.7532	Intermediate Similarity	NPC472956
0.7531	Intermediate Similarity	NPC276356
0.7531	Intermediate Similarity	NPC474510
0.7529	Intermediate Similarity	NPC478145
0.75	Intermediate Similarity	NPC30984
0.75	Intermediate Similarity	NPC318766
0.75	Intermediate Similarity	NPC476598
0.75	Intermediate Similarity	NPC475657
0.75	Intermediate Similarity	NPC261380
0.75	Intermediate Similarity	NPC192006
0.75	Intermediate Similarity	NPC474547
0.75	Intermediate Similarity	NPC196653
0.75	Intermediate Similarity	NPC177932
0.75	Intermediate Similarity	NPC472960
0.75	Intermediate Similarity	NPC471465
0.75	Intermediate Similarity	NPC64234
0.75	Intermediate Similarity	NPC476597
0.75	Intermediate Similarity	NPC37929
0.75	Intermediate Similarity	NPC68110
0.75	Intermediate Similarity	NPC161957
0.75	Intermediate Similarity	NPC255307
0.75	Intermediate Similarity	NPC21471
0.75	Intermediate Similarity	NPC469645
0.75	Intermediate Similarity	NPC184737
0.75	Intermediate Similarity	NPC470755
0.75	Intermediate Similarity	NPC469692
0.75	Intermediate Similarity	NPC33570
0.75	Intermediate Similarity	NPC65661
0.75	Intermediate Similarity	NPC165162
0.75	Intermediate Similarity	NPC472955
0.7471	Intermediate Similarity	NPC144133
0.7471	Intermediate Similarity	NPC62815
0.7471	Intermediate Similarity	NPC253144
0.7471	Intermediate Similarity	NPC312042
0.7471	Intermediate Similarity	NPC473448
0.7471	Intermediate Similarity	NPC179394
0.7471	Intermediate Similarity	NPC51486
0.747	Intermediate Similarity	NPC16488
0.747	Intermediate Similarity	NPC59097
0.747	Intermediate Similarity	NPC131669
0.747	Intermediate Similarity	NPC473390

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 NPC294434 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	1985
0.2-0.3	4146
0.3-0.4	2058
0.4-0.5	537
0.5-0.6	199
0.6-0.7	45
0.7-0.8	5
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
0.8	Intermediate Similarity	NPD5209	Approved
0.7778	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1694	Approved
0.7273	Intermediate Similarity	NPD5785	Approved
0.7093	Intermediate Similarity	NPD5363	Approved
0.7093	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6867	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD5786	Approved
0.6778	Remote Similarity	NPD1695	Approved
0.6744	Remote Similarity	NPD4270	Approved
0.6744	Remote Similarity	NPD4269	Approved
0.6737	Remote Similarity	NPD4225	Approved
0.6707	Remote Similarity	NPD8039	Approved
0.6706	Remote Similarity	NPD4252	Approved
0.6706	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6703	Remote Similarity	NPD6698	Approved
0.6703	Remote Similarity	NPD46	Approved
0.6667	Remote Similarity	NPD7154	Phase 3
0.6667	Remote Similarity	NPD5362	Discontinued
0.6667	Remote Similarity	NPD6927	Phase 3
0.6629	Remote Similarity	NPD7521	Approved
0.6629	Remote Similarity	NPD7146	Approved
0.6629	Remote Similarity	NPD6409	Approved
0.6629	Remote Similarity	NPD7334	Approved
0.6629	Remote Similarity	NPD6684	Approved
0.6629	Remote Similarity	NPD5330	Approved
0.6628	Remote Similarity	NPD5369	Approved
0.6591	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD7638	Approved
0.6562	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6552	Remote Similarity	NPD6435	Approved
0.6522	Remote Similarity	NPD7838	Discovery
0.6512	Remote Similarity	NPD4819	Approved
0.6512	Remote Similarity	NPD4821	Approved
0.6512	Remote Similarity	NPD4822	Approved
0.6512	Remote Similarity	NPD4820	Approved
0.6495	Remote Similarity	NPD7639	Approved
0.6495	Remote Similarity	NPD7640	Approved
0.6489	Remote Similarity	NPD7900	Approved
0.6489	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD6903	Approved
0.6484	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6484	Remote Similarity	NPD5737	Approved
0.6484	Remote Similarity	NPD6672	Approved
0.6477	Remote Similarity	NPD5331	Approved
0.6477	Remote Similarity	NPD5332	Approved
0.6471	Remote Similarity	NPD4271	Approved
0.6471	Remote Similarity	NPD4268	Approved
0.6452	Remote Similarity	NPD5693	Phase 1
0.6437	Remote Similarity	NPD4790	Discontinued
0.6436	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD6371	Approved
0.6383	Remote Similarity	NPD6399	Phase 3
0.6373	Remote Similarity	NPD6686	Approved
0.6322	Remote Similarity	NPD5368	Approved
0.6292	Remote Similarity	NPD6110	Phase 1
0.6289	Remote Similarity	NPD7902	Approved
0.6282	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD4249	Approved
0.6237	Remote Similarity	NPD6051	Approved
0.6196	Remote Similarity	NPD4251	Approved
0.6196	Remote Similarity	NPD4250	Approved
0.6163	Remote Similarity	NPD4756	Discovery
0.6146	Remote Similarity	NPD7748	Approved
0.6139	Remote Similarity	NPD6647	Phase 2
0.6117	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6105	Remote Similarity	NPD7637	Suspended
0.6104	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6082	Remote Similarity	NPD5695	Phase 3
0.6064	Remote Similarity	NPD5370	Suspended
0.6064	Remote Similarity	NPD6080	Approved
0.6064	Remote Similarity	NPD6904	Approved
0.6064	Remote Similarity	NPD6673	Approved
0.6061	Remote Similarity	NPD5696	Approved
0.6055	Remote Similarity	NPD7115	Discovery
0.6042	Remote Similarity	NPD5778	Approved
0.6042	Remote Similarity	NPD5779	Approved
0.6022	Remote Similarity	NPD3573	Approved
0.6	Remote Similarity	NPD6648	Approved
0.6	Remote Similarity	NPD5692	Phase 3
0.6	Remote Similarity	NPD5207	Approved
0.6	Remote Similarity	NPD5343	Approved
0.5979	Remote Similarity	NPD5282	Discontinued
0.596	Remote Similarity	NPD6083	Phase 2
0.596	Remote Similarity	NPD6084	Phase 2
0.5957	Remote Similarity	NPD5208	Approved
0.5946	Remote Similarity	NPD9298	Approved
0.5943	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5943	Remote Similarity	NPD2067	Discontinued
0.5941	Remote Similarity	NPD5344	Discontinued
0.5938	Remote Similarity	NPD7983	Approved
0.5938	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.5938	Remote Similarity	NPD7515	Phase 2
0.5938	Remote Similarity	NPD5694	Approved
0.5938	Remote Similarity	NPD6050	Approved
0.5926	Remote Similarity	NPD7331	Phase 2
0.5914	Remote Similarity	NPD3618	Phase 1
0.5895	Remote Similarity	NPD6101	Approved
0.5895	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5888	Remote Similarity	NPD6649	Approved
0.5888	Remote Similarity	NPD6650	Approved
0.5882	Remote Similarity	NPD7632	Discontinued
0.587	Remote Similarity	NPD3665	Phase 1
0.587	Remote Similarity	NPD3133	Approved
0.587	Remote Similarity	NPD3666	Approved
0.5865	Remote Similarity	NPD6008	Approved
0.5849	Remote Similarity	NPD6372	Approved
0.5849	Remote Similarity	NPD6373	Approved
0.5833	Remote Similarity	NPD6053	Discontinued
0.5833	Remote Similarity	NPD4691	Approved
0.5824	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5823	Remote Similarity	NPD368	Approved
0.5816	Remote Similarity	NPD6001	Approved
0.581	Remote Similarity	NPD5697	Approved
0.5778	Remote Similarity	NPD4695	Discontinued
0.5773	Remote Similarity	NPD6411	Approved
0.5773	Remote Similarity	NPD5281	Approved
0.5773	Remote Similarity	NPD5284	Approved
0.5755	Remote Similarity	NPD6881	Approved
0.5755	Remote Similarity	NPD6899	Approved
0.5755	Remote Similarity	NPD6011	Approved
0.5747	Remote Similarity	NPD1452	Discontinued
0.5745	Remote Similarity	NPD6098	Approved
0.5745	Remote Similarity	NPD5279	Phase 3
0.5745	Remote Similarity	NPD6422	Discontinued
0.5732	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.5714	Remote Similarity	NPD7128	Approved
0.5714	Remote Similarity	NPD6675	Approved
0.5714	Remote Similarity	NPD5739	Approved
0.5714	Remote Similarity	NPD3174	Discontinued
0.5714	Remote Similarity	NPD4137	Phase 3
0.5714	Remote Similarity	NPD6402	Approved
0.5701	Remote Similarity	NPD6013	Approved
0.5701	Remote Similarity	NPD6012	Approved
0.5701	Remote Similarity	NPD6413	Approved
0.5701	Remote Similarity	NPD2182	Approved
0.5701	Remote Similarity	NPD6014	Approved
0.5701	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.57	Remote Similarity	NPD4697	Phase 3
0.57	Remote Similarity	NPD7839	Suspended
0.5699	Remote Similarity	NPD3668	Phase 3
0.5663	Remote Similarity	NPD4247	Clinical (unspecified phase)
0.566	Remote Similarity	NPD5701	Approved
0.5652	Remote Similarity	NPD3667	Approved
0.5648	Remote Similarity	NPD7290	Approved
0.5648	Remote Similarity	NPD6883	Approved
0.5648	Remote Similarity	NPD7102	Approved
0.5647	Remote Similarity	NPD4747	Approved
0.5641	Remote Similarity	NPD287	Approved
0.5638	Remote Similarity	NPD1696	Phase 3
0.5632	Remote Similarity	NPD4058	Approved
0.5625	Remote Similarity	NPD4193	Approved
0.5625	Remote Similarity	NPD4192	Approved
0.5625	Remote Similarity	NPD4194	Approved
0.5625	Remote Similarity	NPD4191	Approved
0.5612	Remote Similarity	NPD6079	Approved
0.5612	Remote Similarity	NPD8035	Phase 2
0.5612	Remote Similarity	NPD8034	Phase 2
0.561	Remote Similarity	NPD7341	Phase 2
0.5607	Remote Similarity	NPD7320	Approved
0.5604	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.56	Remote Similarity	NPD5654	Approved
0.56	Remote Similarity	NPD5210	Approved
0.56	Remote Similarity	NPD4629	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