NPASS Compound

Structure

NPC180290 OpenBabel07101718292D 23 24 0 0 1 0 0 0 0 0999 V2000 1.4787 -4.7492 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1085 -4.4165 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5614 -0.9667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4666 1.4570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0017 -0.0952 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0120 -1.1135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4501 -1.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3000 -0.1330 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8731 -2.7597 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0458 -3.1327 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2141 -2.6525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6074 0.5323 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2744 0.6176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1976 -4.1123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6041 -1.0439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0055 -3.1714 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2992 -1.8408 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6849 0.7995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3764 -0.8835 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7439 0.6074 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7236 1.7591 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3244 -0.7295 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 14 1 0 0 0 0 2 14 1 0 0 0 0 3 15 1 0 0 0 0 5 6 1 0 0 0 0 5 13 1 0 0 0 0 6 17 2 0 0 0 0 7 9 1 0 0 0 0 7 15 2 0 0 0 0 8 12 1 0 0 0 0 8 15 1 0 0 0 0 9 16 2 0 0 0 0 10 11 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 12 18 1 0 0 0 0 13 20 1 0 0 0 0 14 16 1 0 0 0 0 17 19 1 0 0 0 0 18 20 1 0 0 0 0 18 21 2 0 0 0 0 19 22 2 0 0 0 0 19 23 1 0 0 0 0 20 4 1 6 0 0 0 20 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	316.2
Volume:	350.552
LogP:	3.557
LogD:	3.381
LogS:	-4.171
# Rotatable Bonds:	1
TPSA:	43.37
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.66
Synthetic Accessibility Score:	5.117
Fsp3:	0.6
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:	-4.571
MDCK Permeability:	2.8628654035856016e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.486
30% Bioavailability (F30%):	0.22

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.132
Plasma Protein Binding (PPB):	96.4720230102539%
Volume Distribution (VD):	1.375
Pgp-substrate:	3.7495601177215576%

ADMET: Metabolism

CYP1A2-inhibitor:	0.566
CYP1A2-substrate:	0.63
CYP2C19-inhibitor:	0.706
CYP2C19-substrate:	0.903
CYP2C9-inhibitor:	0.706
CYP2C9-substrate:	0.14
CYP2D6-inhibitor:	0.52
CYP2D6-substrate:	0.088
CYP3A4-inhibitor:	0.918
CYP3A4-substrate:	0.649

ADMET: Excretion

Clearance (CL):	6.769
Half-life (T1/2):	0.734

ADMET: Toxicity

hERG Blockers:	0.063
Human Hepatotoxicity (H-HT):	0.91
Drug-inuced Liver Injury (DILI):	0.224
AMES Toxicity:	0.171
Rat Oral Acute Toxicity:	0.441
Maximum Recommended Daily Dose:	0.927
Skin Sensitization:	0.788
Carcinogencity:	0.887
Eye Corrosion:	0.004
Eye Irritation:	0.021
Respiratory Toxicity:	0.886

Download Data

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

Natural Product: NPC180290

Natural Product ID:	NPC180290
*Common Name:**	4Z,12Z,14E-Sarcophytolide
IUPAC Name:	(4E,6Z,11S)-7,11-dimethyl-4-propan-2-yl-16-oxabicyclo[9.3.2]hexadeca-1(14),4,6-triene-10,15-dione
Synonyms:
Standard InCHIKey:	PSZUHEPXMXTNIL-VYZDZDEQSA-N
Standard InCHI:	InChI=1S/C20H28O3/c1-14(2)16-9-7-15(3)8-12-18(21)20(4)13-5-6-17(11-10-16)19(22)23-20/h6-7,9,14H,5,8,10-13H2,1-4H3/b15-7-,16-9+/t20-/m0/s1
SMILES:	CC(C)/C/1=C/C=C(/C)CCC(=O)[C@]2(C)CCC=C(CC1)C(=O)O2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2414205
PubChem CID:	11381519
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	=	15400.0	nM	PMID[455596]

☑ 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 NPC180290 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	269
0.1-0.2	1555
0.2-0.3	6970
0.3-0.4	16321
0.4-0.5	10425
0.5-0.6	5269
0.6-0.7	1668
0.7-0.8	214
0.8-0.85	3
0.85-0.9	0
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9342	High Similarity	NPC221231
0.9342	High Similarity	NPC471326
0.8072	Intermediate Similarity	NPC99395
0.8072	Intermediate Similarity	NPC197903
0.8	Intermediate Similarity	NPC264227
0.8	Intermediate Similarity	NPC63649
0.8	Intermediate Similarity	NPC472965
0.8	Intermediate Similarity	NPC265574
0.7976	Intermediate Similarity	NPC38576
0.7976	Intermediate Similarity	NPC279859
0.7975	Intermediate Similarity	NPC316324
0.7949	Intermediate Similarity	NPC244166
0.7931	Intermediate Similarity	NPC45579
0.7927	Intermediate Similarity	NPC474291
0.7875	Intermediate Similarity	NPC128276
0.7831	Intermediate Similarity	NPC474703
0.7831	Intermediate Similarity	NPC170377
0.7805	Intermediate Similarity	NPC42470
0.7792	Intermediate Similarity	NPC288667
0.7791	Intermediate Similarity	NPC469631
0.7791	Intermediate Similarity	NPC475906
0.7791	Intermediate Similarity	NPC471047
0.7791	Intermediate Similarity	NPC469653
0.7791	Intermediate Similarity	NPC469628
0.7765	Intermediate Similarity	NPC234038
0.7763	Intermediate Similarity	NPC232812
0.775	Intermediate Similarity	NPC65603
0.775	Intermediate Similarity	NPC57744
0.7738	Intermediate Similarity	NPC196487
0.7738	Intermediate Similarity	NPC14575
0.7738	Intermediate Similarity	NPC474359
0.7727	Intermediate Similarity	NPC166110
0.7722	Intermediate Similarity	NPC226669
0.7722	Intermediate Similarity	NPC193351
0.7722	Intermediate Similarity	NPC138408
0.7711	Intermediate Similarity	NPC85772
0.7703	Intermediate Similarity	NPC470688
0.7683	Intermediate Similarity	NPC474510
0.7671	Intermediate Similarity	NPC155849
0.7662	Intermediate Similarity	NPC67183
0.7662	Intermediate Similarity	NPC64234
0.7662	Intermediate Similarity	NPC37929
0.7654	Intermediate Similarity	NPC299235
0.7654	Intermediate Similarity	NPC471220
0.764	Intermediate Similarity	NPC248193
0.7625	Intermediate Similarity	NPC473223
0.7625	Intermediate Similarity	NPC472967
0.7625	Intermediate Similarity	NPC40353
0.7625	Intermediate Similarity	NPC266159
0.76	Intermediate Similarity	NPC142423
0.76	Intermediate Similarity	NPC308294
0.7595	Intermediate Similarity	NPC476355
0.759	Intermediate Similarity	NPC301477
0.759	Intermediate Similarity	NPC25684
0.759	Intermediate Similarity	NPC471325
0.759	Intermediate Similarity	NPC281949
0.7586	Intermediate Similarity	NPC475902
0.7582	Intermediate Similarity	NPC299396
0.7582	Intermediate Similarity	NPC301596
0.7582	Intermediate Similarity	NPC172998
0.7564	Intermediate Similarity	NPC163003
0.7561	Intermediate Similarity	NPC178277
0.7561	Intermediate Similarity	NPC469617
0.7558	Intermediate Similarity	NPC261721
0.7558	Intermediate Similarity	NPC122502
0.7531	Intermediate Similarity	NPC470240
0.7531	Intermediate Similarity	NPC187568
0.7531	Intermediate Similarity	NPC476794
0.7531	Intermediate Similarity	NPC41780
0.7528	Intermediate Similarity	NPC193396
0.7528	Intermediate Similarity	NPC32944
0.75	Intermediate Similarity	NPC21998
0.75	Intermediate Similarity	NPC173609
0.75	Intermediate Similarity	NPC142159
0.75	Intermediate Similarity	NPC95364
0.75	Intermediate Similarity	NPC155587
0.7473	Intermediate Similarity	NPC234339
0.7473	Intermediate Similarity	NPC273197
0.7473	Intermediate Similarity	NPC474490
0.7471	Intermediate Similarity	NPC478145
0.747	Intermediate Similarity	NPC47747
0.747	Intermediate Similarity	NPC302426
0.747	Intermediate Similarity	NPC304795
0.7442	Intermediate Similarity	NPC96621
0.7442	Intermediate Similarity	NPC261380
0.7436	Intermediate Similarity	NPC316029
0.7436	Intermediate Similarity	NPC475310
0.7416	Intermediate Similarity	NPC471818
0.7412	Intermediate Similarity	NPC53867
0.7412	Intermediate Similarity	NPC318468
0.7412	Intermediate Similarity	NPC475989
0.7412	Intermediate Similarity	NPC222358
0.7407	Intermediate Similarity	NPC27205
0.7407	Intermediate Similarity	NPC235906
0.7407	Intermediate Similarity	NPC123360
0.7403	Intermediate Similarity	NPC218477
0.7381	Intermediate Similarity	NPC325031
0.7381	Intermediate Similarity	NPC286229
0.7381	Intermediate Similarity	NPC141810
0.7375	Intermediate Similarity	NPC259599
0.7375	Intermediate Similarity	NPC15499
0.7375	Intermediate Similarity	NPC474758
0.7375	Intermediate Similarity	NPC140287
0.7375	Intermediate Similarity	NPC117746
0.7375	Intermediate Similarity	NPC294434
0.7363	Intermediate Similarity	NPC469632
0.7356	Intermediate Similarity	NPC472863
0.7356	Intermediate Similarity	NPC107787
0.7356	Intermediate Similarity	NPC164393
0.7349	Intermediate Similarity	NPC270126
0.7349	Intermediate Similarity	NPC471740
0.7349	Intermediate Similarity	NPC469690
0.7349	Intermediate Similarity	NPC617
0.7333	Intermediate Similarity	NPC20713
0.7333	Intermediate Similarity	NPC219874
0.7326	Intermediate Similarity	NPC115786
0.7326	Intermediate Similarity	NPC475100
0.7326	Intermediate Similarity	NPC149869
0.7317	Intermediate Similarity	NPC53581
0.7317	Intermediate Similarity	NPC122264
0.7317	Intermediate Similarity	NPC103987
0.7317	Intermediate Similarity	NPC471225
0.7308	Intermediate Similarity	NPC470693
0.7303	Intermediate Similarity	NPC115179
0.7303	Intermediate Similarity	NPC212598
0.7303	Intermediate Similarity	NPC106040
0.7284	Intermediate Similarity	NPC469414
0.7284	Intermediate Similarity	NPC228978
0.7284	Intermediate Similarity	NPC329826
0.7284	Intermediate Similarity	NPC329852
0.7273	Intermediate Similarity	NPC472266
0.7273	Intermediate Similarity	NPC278895
0.7273	Intermediate Similarity	NPC478144
0.7262	Intermediate Similarity	NPC233377
0.7262	Intermediate Similarity	NPC74673
0.7262	Intermediate Similarity	NPC69271
0.725	Intermediate Similarity	NPC135703
0.725	Intermediate Similarity	NPC295633
0.725	Intermediate Similarity	NPC287878
0.725	Intermediate Similarity	NPC269206
0.725	Intermediate Similarity	NPC58956
0.7241	Intermediate Similarity	NPC78089
0.7241	Intermediate Similarity	NPC189311
0.7241	Intermediate Similarity	NPC474547
0.7241	Intermediate Similarity	NPC470177
0.7229	Intermediate Similarity	NPC222210
0.7229	Intermediate Similarity	NPC315765
0.7229	Intermediate Similarity	NPC99182
0.7229	Intermediate Similarity	NPC63445
0.7229	Intermediate Similarity	NPC267231
0.7229	Intermediate Similarity	NPC472960
0.7229	Intermediate Similarity	NPC474341
0.7229	Intermediate Similarity	NPC108816
0.7229	Intermediate Similarity	NPC93763
0.7222	Intermediate Similarity	NPC329857
0.7222	Intermediate Similarity	NPC469718
0.7215	Intermediate Similarity	NPC469660
0.7209	Intermediate Similarity	NPC288281
0.7209	Intermediate Similarity	NPC16488
0.7209	Intermediate Similarity	NPC39588
0.7209	Intermediate Similarity	NPC193198
0.7209	Intermediate Similarity	NPC475947
0.7204	Intermediate Similarity	NPC473291
0.7195	Intermediate Similarity	NPC474527
0.7195	Intermediate Similarity	NPC471726
0.7191	Intermediate Similarity	NPC473658
0.7191	Intermediate Similarity	NPC241507
0.7188	Intermediate Similarity	NPC189609
0.7188	Intermediate Similarity	NPC197835
0.7188	Intermediate Similarity	NPC140591
0.7188	Intermediate Similarity	NPC291500
0.7188	Intermediate Similarity	NPC303653
0.7179	Intermediate Similarity	NPC470256
0.7179	Intermediate Similarity	NPC476614
0.7179	Intermediate Similarity	NPC276290
0.7179	Intermediate Similarity	NPC313444
0.7179	Intermediate Similarity	NPC134385
0.7176	Intermediate Similarity	NPC112868
0.7176	Intermediate Similarity	NPC10276
0.7176	Intermediate Similarity	NPC35089
0.7174	Intermediate Similarity	NPC121825
0.7174	Intermediate Similarity	NPC148463
0.7174	Intermediate Similarity	NPC476596
0.716	Intermediate Similarity	NPC20025
0.7159	Intermediate Similarity	NPC315395
0.7159	Intermediate Similarity	NPC316426
0.7159	Intermediate Similarity	NPC261253
0.7159	Intermediate Similarity	NPC474045
0.7143	Intermediate Similarity	NPC191233
0.7143	Intermediate Similarity	NPC472705
0.7143	Intermediate Similarity	NPC470239
0.7143	Intermediate Similarity	NPC470244
0.7143	Intermediate Similarity	NPC469620
0.7143	Intermediate Similarity	NPC182550
0.7126	Intermediate Similarity	NPC30486
0.7126	Intermediate Similarity	NPC238197
0.7126	Intermediate Similarity	NPC243618
0.7126	Intermediate Similarity	NPC70424
0.7125	Intermediate Similarity	NPC84038
0.7125	Intermediate Similarity	NPC186531

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 NPC180290 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	258
0.1-0.2	1946
0.2-0.3	3954
0.3-0.4	2055
0.4-0.5	678
0.5-0.6	221
0.6-0.7	36
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
0.7317	Intermediate Similarity	NPD4756	Discovery
0.7284	Intermediate Similarity	NPD8039	Approved
0.7237	Intermediate Similarity	NPD2685	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD5693	Phase 1
0.7093	Intermediate Similarity	NPD5209	Approved
0.7093	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7033	Intermediate Similarity	NPD5692	Phase 3
0.6957	Remote Similarity	NPD6050	Approved
0.6957	Remote Similarity	NPD5694	Approved
0.6854	Remote Similarity	NPD1694	Approved
0.6739	Remote Similarity	NPD6673	Approved
0.6739	Remote Similarity	NPD6080	Approved
0.6739	Remote Similarity	NPD6904	Approved
0.6709	Remote Similarity	NPD7331	Phase 2
0.6709	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.663	Remote Similarity	NPD6672	Approved
0.663	Remote Similarity	NPD5737	Approved
0.6593	Remote Similarity	NPD6098	Approved
0.6562	Remote Similarity	NPD5654	Approved
0.6559	Remote Similarity	NPD1695	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6489	Remote Similarity	NPD46	Approved
0.6489	Remote Similarity	NPD5785	Approved
0.6489	Remote Similarity	NPD5207	Approved
0.6489	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD5959	Approved
0.6408	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6392	Remote Similarity	NPD5695	Phase 3
0.6392	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6375	Remote Similarity	NPD7341	Phase 2
0.6329	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD7838	Discovery
0.6304	Remote Similarity	NPD5363	Approved
0.6292	Remote Similarity	NPD4695	Discontinued
0.6277	Remote Similarity	NPD5208	Approved
0.6264	Remote Similarity	NPD7154	Phase 3
0.6263	Remote Similarity	NPD6083	Phase 2
0.6263	Remote Similarity	NPD6084	Phase 2
0.625	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6237	Remote Similarity	NPD6684	Approved
0.6237	Remote Similarity	NPD4694	Approved
0.6237	Remote Similarity	NPD7521	Approved
0.6237	Remote Similarity	NPD7334	Approved
0.6237	Remote Similarity	NPD7146	Approved
0.6237	Remote Similarity	NPD5280	Approved
0.6237	Remote Similarity	NPD6409	Approved
0.6237	Remote Similarity	NPD5330	Approved
0.6211	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.62	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.62	Remote Similarity	NPD5696	Approved
0.6164	Remote Similarity	NPD28	Approved
0.6164	Remote Similarity	NPD29	Approved
0.6105	Remote Similarity	NPD6903	Approved
0.6105	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5362	Discontinued
0.6082	Remote Similarity	NPD7983	Approved
0.6082	Remote Similarity	NPD5284	Approved
0.6082	Remote Similarity	NPD5281	Approved
0.6075	Remote Similarity	NPD2067	Discontinued
0.6075	Remote Similarity	NPD6371	Approved
0.6067	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD5279	Phase 3
0.6064	Remote Similarity	NPD5690	Phase 2
0.6058	Remote Similarity	NPD5909	Discontinued
0.6044	Remote Similarity	NPD5369	Approved
0.6022	Remote Similarity	NPD4197	Approved
0.602	Remote Similarity	NPD5778	Approved
0.602	Remote Similarity	NPD5779	Approved
0.6	Remote Similarity	NPD4194	Approved
0.6	Remote Similarity	NPD3172	Approved
0.6	Remote Similarity	NPD4193	Approved
0.6	Remote Similarity	NPD4192	Approved
0.6	Remote Similarity	NPD4191	Approved
0.5978	Remote Similarity	NPD4269	Approved
0.5978	Remote Similarity	NPD4270	Approved
0.5978	Remote Similarity	NPD6435	Approved
0.5978	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD4058	Approved
0.596	Remote Similarity	NPD6001	Approved
0.5957	Remote Similarity	NPD1696	Phase 3
0.5957	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.5957	Remote Similarity	NPD5329	Approved
0.5946	Remote Similarity	NPD690	Clinical (unspecified phase)
0.5946	Remote Similarity	NPD6927	Phase 3
0.5943	Remote Similarity	NPD5697	Approved
0.5943	Remote Similarity	NPD6614	Approved
0.593	Remote Similarity	NPD5276	Approved
0.5921	Remote Similarity	NPD3196	Approved
0.5921	Remote Similarity	NPD4266	Approved
0.5921	Remote Similarity	NPD3194	Approved
0.5921	Remote Similarity	NPD3195	Phase 2
0.5904	Remote Similarity	NPD3704	Approved
0.59	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.5895	Remote Similarity	NPD4623	Approved
0.5895	Remote Similarity	NPD4519	Discontinued
0.5895	Remote Similarity	NPD5786	Approved
0.5888	Remote Similarity	NPD6881	Approved
0.5888	Remote Similarity	NPD6011	Approved
0.5888	Remote Similarity	NPD6899	Approved
0.5876	Remote Similarity	NPD6101	Approved
0.5876	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.5854	Remote Similarity	NPD3197	Phase 1
0.5849	Remote Similarity	NPD5739	Approved
0.5849	Remote Similarity	NPD7128	Approved
0.5849	Remote Similarity	NPD6675	Approved
0.5849	Remote Similarity	NPD6402	Approved
0.5842	Remote Similarity	NPD7839	Suspended
0.5833	Remote Similarity	NPD6013	Approved
0.5833	Remote Similarity	NPD6012	Approved
0.5833	Remote Similarity	NPD6014	Approved
0.5825	Remote Similarity	NPD6648	Approved
0.5814	Remote Similarity	NPD4691	Approved
0.5806	Remote Similarity	NPD4221	Approved
0.5806	Remote Similarity	NPD4223	Phase 3
0.58	Remote Similarity	NPD5282	Discontinued
0.58	Remote Similarity	NPD5122	Clinical (unspecified phase)
0.58	Remote Similarity	NPD7748	Approved
0.58	Remote Similarity	NPD7900	Approved
0.58	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.5795	Remote Similarity	NPD5733	Approved
0.5795	Remote Similarity	NPD4687	Approved
0.5794	Remote Similarity	NPD5701	Approved
0.578	Remote Similarity	NPD6883	Approved
0.578	Remote Similarity	NPD7102	Approved
0.578	Remote Similarity	NPD7290	Approved
0.5773	Remote Similarity	NPD4518	Approved
0.5761	Remote Similarity	NPD4821	Approved
0.5761	Remote Similarity	NPD4819	Approved
0.5761	Remote Similarity	NPD5368	Approved
0.5761	Remote Similarity	NPD4820	Approved
0.5761	Remote Similarity	NPD4822	Approved
0.5761	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.5761	Remote Similarity	NPD4252	Approved
0.5758	Remote Similarity	NPD6411	Approved
0.5741	Remote Similarity	NPD7320	Approved
0.5741	Remote Similarity	NPD6686	Approved
0.573	Remote Similarity	NPD1452	Discontinued
0.5728	Remote Similarity	NPD4225	Approved
0.5728	Remote Similarity	NPD7638	Approved
0.5727	Remote Similarity	NPD6649	Approved
0.5727	Remote Similarity	NPD6617	Approved
0.5727	Remote Similarity	NPD2181	Clinical (unspecified phase)
0.5727	Remote Similarity	NPD8130	Phase 1
0.5727	Remote Similarity	NPD6869	Approved
0.5727	Remote Similarity	NPD6847	Approved
0.5727	Remote Similarity	NPD6650	Approved
0.5714	Remote Similarity	NPD3617	Approved
0.5714	Remote Similarity	NPD4753	Phase 2
0.57	Remote Similarity	NPD5133	Approved
0.5698	Remote Similarity	NPD4137	Phase 3
0.5694	Remote Similarity	NPD3174	Discontinued
0.5688	Remote Similarity	NPD6373	Approved
0.5688	Remote Similarity	NPD6372	Approved
0.5679	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.5676	Remote Similarity	NPD6053	Discontinued
0.5676	Remote Similarity	NPD8297	Approved
0.5676	Remote Similarity	NPD6882	Approved
0.5673	Remote Similarity	NPD7639	Approved
0.5673	Remote Similarity	NPD6404	Discontinued
0.5673	Remote Similarity	NPD7640	Approved
0.5673	Remote Similarity	NPD2066	Phase 3
0.566	Remote Similarity	NPD6647	Phase 2
0.5657	Remote Similarity	NPD3673	Approved
0.5657	Remote Similarity	NPD3672	Approved
0.5657	Remote Similarity	NPD4096	Approved
0.5632	Remote Similarity	NPD4747	Approved
0.5631	Remote Similarity	NPD7902	Approved
0.5614	Remote Similarity	NPD7115	Discovery
0.5603	Remote Similarity	NPD7299	Clinical (unspecified phase)
0.56	Remote Similarity	NPD7515	Phase 2

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