NPASS Compound

Structure

NPC261721 OpenBabel07101718282D 24 25 0 0 1 0 0 0 0 0999 V2000 1.7851 2.8258 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2168 3.3353 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0818 -1.7741 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0177 1.7793 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5005 1.6109 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5005 -0.6588 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5596 -0.7702 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0315 1.4499 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4651 0.4760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4651 0.4760 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8538 2.6278 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0177 -0.8272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5596 1.7223 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9055 1.2463 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3518 1.0090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9055 -0.2942 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0315 -0.4978 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3518 -0.0570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 0.9521 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2216 1.3963 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6686 -1.2053 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2216 -0.4442 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5405 2.0713 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 11 2 0 0 0 0 2 11 1 0 0 0 0 3 12 1 0 0 0 0 4 5 1 0 0 0 0 4 13 1 0 0 0 0 5 14 1 0 0 0 0 6 12 1 0 0 0 0 7 12 2 0 0 0 0 7 17 1 0 0 0 0 8 13 1 0 0 0 0 8 15 1 0 0 0 0 9 14 2 0 0 0 0 9 16 1 0 0 0 0 10 15 1 0 0 0 0 10 18 1 0 0 0 0 13 11 1 6 0 0 0 14 19 1 0 0 0 0 15 20 2 0 0 0 0 16 6 1 6 0 0 0 16 24 1 0 0 0 0 17 18 1 0 0 0 0 17 21 2 0 0 0 0 18 22 1 1 0 0 0 19 23 2 0 0 0 0 19 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	332.16
Volume:	348.2
LogP:	2.764
LogD:	2.11
LogS:	-4.011
# Rotatable Bonds:	1
TPSA:	84.58
# H-Bond Aceptor:	5
# H-Bond Donor:	1
# Rings:	2
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.485
Synthetic Accessibility Score:	5.35
Fsp3:	0.526
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.699
MDCK Permeability:	2.541364483477082e-05
Pgp-inhibitor:	0.015
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.145
20% Bioavailability (F20%):	0.051
30% Bioavailability (F30%):	0.002

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.009
Plasma Protein Binding (PPB):	76.51721954345703%
Volume Distribution (VD):	0.329
Pgp-substrate:	14.560885429382324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.049
CYP1A2-substrate:	0.338
CYP2C19-inhibitor:	0.095
CYP2C19-substrate:	0.098
CYP2C9-inhibitor:	0.228
CYP2C9-substrate:	0.942
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.472
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	12.263
Half-life (T1/2):	0.832

ADMET: Toxicity

hERG Blockers:	0.005
Human Hepatotoxicity (H-HT):	0.184
Drug-inuced Liver Injury (DILI):	0.672
AMES Toxicity:	0.047
Rat Oral Acute Toxicity:	0.422
Maximum Recommended Daily Dose:	0.623
Skin Sensitization:	0.385
Carcinogencity:	0.811
Eye Corrosion:	0.019
Eye Irritation:	0.056
Respiratory Toxicity:	0.955

Download Data

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

Natural Product: NPC261721

Natural Product ID:	NPC261721
*Common Name:**	Gyrosanolide D
IUPAC Name:	(1R,3E,6R,10S)-6-hydroxy-3-methyl-10-prop-1-en-2-yl-15-oxabicyclo[11.2.1]hexadeca-3,13(16)-diene-5,8,14-trione
Synonyms:	Gyrosanolide D
Standard InCHIKey:	NKBOMIIKMNCYIQ-XOYNJCORSA-N
Standard InCHI:	InChI=1S/C19H24O5/c1-11(2)13-4-5-14-9-16(24-19(14)23)6-12(3)7-17(21)18(22)10-15(20)8-13/h7,9,13,16,18,22H,1,4-6,8,10H2,2-3H3/b12-7+/t13-,16+,18+/m0/s1
SMILES:	C=C(C)[C@H]1CCC2=C[C@@H](C/C(=C/C(=O)[C@@H](CC(=O)C1)O)/C)OC2=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1094550
PubChem CID:	46888447
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001983] Dihydrofurans [CHEMONTID:0001982] Furanones [CHEMONTID:0002223] Butenolides

*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
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20430633]
NPO23707	Sinularia gyrosa	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[20499851]
NPO23707	Sinularia gyrosa	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
ED50	4

Activity Type	# Activity
Cell Line	3
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	ED50	>	20.0	ug ml-1	PMID[535857]
NPT139	Cell Line	HT-29	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[535857]
NPT81	Cell Line	A549	Homo sapiens	ED50	>	20.0	ug ml-1	PMID[535857]
NPT1750	Organism	Human herpesvirus 5	Human herpesvirus 5	ED50	>	50.0	ug ml-1	PMID[535857]

☑ 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 NPC261721 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	202
0.1-0.2	1166
0.2-0.3	4963
0.3-0.4	10223
0.4-0.5	14252
0.5-0.6	6796
0.6-0.7	3856
0.7-0.8	1147
0.8-0.85	84
0.85-0.9	7
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.908	High Similarity	NPC469645
0.908	High Similarity	NPC469692
0.8977	High Similarity	NPC121825
0.8977	High Similarity	NPC469632
0.8706	High Similarity	NPC261380
0.8652	High Similarity	NPC475302
0.8621	High Similarity	NPC469631
0.8621	High Similarity	NPC475906
0.8621	High Similarity	NPC469653
0.8621	High Similarity	NPC471047
0.8621	High Similarity	NPC469628
0.8605	High Similarity	NPC38576
0.8605	High Similarity	NPC279859
0.8537	High Similarity	NPC128276
0.8452	Intermediate Similarity	NPC471325
0.8452	Intermediate Similarity	NPC325031
0.8434	Intermediate Similarity	NPC178277
0.8427	Intermediate Similarity	NPC51486
0.8415	Intermediate Similarity	NPC57744
0.8409	Intermediate Similarity	NPC475902
0.8404	Intermediate Similarity	NPC110443
0.8404	Intermediate Similarity	NPC46998
0.8404	Intermediate Similarity	NPC133907
0.8404	Intermediate Similarity	NPC128733
0.8404	Intermediate Similarity	NPC185141
0.8391	Intermediate Similarity	NPC475461
0.8391	Intermediate Similarity	NPC469483
0.8391	Intermediate Similarity	NPC305475
0.8372	Intermediate Similarity	NPC82297
0.8353	Intermediate Similarity	NPC85772
0.8333	Intermediate Similarity	NPC219874
0.8315	Intermediate Similarity	NPC295312
0.8313	Intermediate Similarity	NPC108816
0.8313	Intermediate Similarity	NPC93763
0.8276	Intermediate Similarity	NPC165162
0.8276	Intermediate Similarity	NPC470755
0.8276	Intermediate Similarity	NPC255307
0.8261	Intermediate Similarity	NPC209355
0.8256	Intermediate Similarity	NPC16488
0.8235	Intermediate Similarity	NPC112868
0.8235	Intermediate Similarity	NPC42470
0.8222	Intermediate Similarity	NPC145666
0.8214	Intermediate Similarity	NPC470244
0.8214	Intermediate Similarity	NPC470239
0.8202	Intermediate Similarity	NPC476805
0.8193	Intermediate Similarity	NPC7563
0.8193	Intermediate Similarity	NPC320630
0.8193	Intermediate Similarity	NPC116177
0.8182	Intermediate Similarity	NPC150755
0.8182	Intermediate Similarity	NPC315395
0.8182	Intermediate Similarity	NPC316426
0.8172	Intermediate Similarity	NPC473291
0.8161	Intermediate Similarity	NPC114979
0.8161	Intermediate Similarity	NPC96259
0.8161	Intermediate Similarity	NPC158756
0.8161	Intermediate Similarity	NPC191476
0.8161	Intermediate Similarity	NPC141193
0.8152	Intermediate Similarity	NPC53685
0.814	Intermediate Similarity	NPC173609
0.814	Intermediate Similarity	NPC474291
0.8132	Intermediate Similarity	NPC261607
0.8132	Intermediate Similarity	NPC111114
0.8132	Intermediate Similarity	NPC472814
0.8132	Intermediate Similarity	NPC300312
0.8132	Intermediate Similarity	NPC177037
0.8125	Intermediate Similarity	NPC67183
0.8111	Intermediate Similarity	NPC5509
0.8111	Intermediate Similarity	NPC268298
0.809	Intermediate Similarity	NPC160138
0.809	Intermediate Similarity	NPC312561
0.809	Intermediate Similarity	NPC72513
0.809	Intermediate Similarity	NPC471738
0.8072	Intermediate Similarity	NPC123360
0.8068	Intermediate Similarity	NPC125290
0.8049	Intermediate Similarity	NPC294434
0.8049	Intermediate Similarity	NPC15499
0.8049	Intermediate Similarity	NPC476355
0.8049	Intermediate Similarity	NPC259599
0.8049	Intermediate Similarity	NPC117746
0.8046	Intermediate Similarity	NPC131669
0.8046	Intermediate Similarity	NPC473390
0.8046	Intermediate Similarity	NPC475947
0.8046	Intermediate Similarity	NPC40746
0.8046	Intermediate Similarity	NPC318468
0.8046	Intermediate Similarity	NPC474703
0.8046	Intermediate Similarity	NPC169575
0.8043	Intermediate Similarity	NPC115021
0.8041	Intermediate Similarity	NPC472755
0.8041	Intermediate Similarity	NPC475945
0.8041	Intermediate Similarity	NPC475871
0.8023	Intermediate Similarity	NPC25684
0.8023	Intermediate Similarity	NPC301477
0.8023	Intermediate Similarity	NPC281949
0.8022	Intermediate Similarity	NPC473448
0.8022	Intermediate Similarity	NPC129419
0.8022	Intermediate Similarity	NPC71533
0.8022	Intermediate Similarity	NPC475879
0.8022	Intermediate Similarity	NPC106510
0.8022	Intermediate Similarity	NPC232426
0.8022	Intermediate Similarity	NPC77337
0.8022	Intermediate Similarity	NPC281942
0.8021	Intermediate Similarity	NPC472753
0.8021	Intermediate Similarity	NPC164598
0.8021	Intermediate Similarity	NPC474339
0.8021	Intermediate Similarity	NPC474742
0.8	Intermediate Similarity	NPC161855
0.8	Intermediate Similarity	NPC141191
0.8	Intermediate Similarity	NPC222011
0.8	Intermediate Similarity	NPC475819
0.8	Intermediate Similarity	NPC476803
0.8	Intermediate Similarity	NPC19841
0.7979	Intermediate Similarity	NPC184065
0.7979	Intermediate Similarity	NPC242848
0.7979	Intermediate Similarity	NPC230800
0.7978	Intermediate Similarity	NPC284902
0.7978	Intermediate Similarity	NPC469910
0.7976	Intermediate Similarity	NPC476794
0.7976	Intermediate Similarity	NPC470240
0.7976	Intermediate Similarity	NPC65603
0.7957	Intermediate Similarity	NPC167219
0.7957	Intermediate Similarity	NPC65829
0.7955	Intermediate Similarity	NPC31086
0.7955	Intermediate Similarity	NPC476804
0.7952	Intermediate Similarity	NPC244166
0.7952	Intermediate Similarity	NPC329852
0.7938	Intermediate Similarity	NPC474747
0.7938	Intermediate Similarity	NPC291500
0.7938	Intermediate Similarity	NPC140591
0.7938	Intermediate Similarity	NPC189609
0.7938	Intermediate Similarity	NPC303653
0.7938	Intermediate Similarity	NPC149371
0.7938	Intermediate Similarity	NPC472754
0.7938	Intermediate Similarity	NPC197835
0.7935	Intermediate Similarity	NPC20713
0.7935	Intermediate Similarity	NPC141831
0.7931	Intermediate Similarity	NPC35556
0.7931	Intermediate Similarity	NPC229825
0.7931	Intermediate Similarity	NPC89555
0.7917	Intermediate Similarity	NPC474012
0.7917	Intermediate Similarity	NPC476299
0.7912	Intermediate Similarity	NPC212598
0.7907	Intermediate Similarity	NPC223904
0.7895	Intermediate Similarity	NPC169205
0.7895	Intermediate Similarity	NPC475709
0.7895	Intermediate Similarity	NPC53844
0.7895	Intermediate Similarity	NPC208094
0.7895	Intermediate Similarity	NPC477949
0.7895	Intermediate Similarity	NPC69385
0.7889	Intermediate Similarity	NPC478144
0.7882	Intermediate Similarity	NPC267231
0.7882	Intermediate Similarity	NPC471465
0.7882	Intermediate Similarity	NPC192006
0.7882	Intermediate Similarity	NPC196653
0.7882	Intermediate Similarity	NPC299235
0.7872	Intermediate Similarity	NPC295347
0.7872	Intermediate Similarity	NPC48803
0.7872	Intermediate Similarity	NPC193645
0.7872	Intermediate Similarity	NPC275960
0.7872	Intermediate Similarity	NPC476487
0.7872	Intermediate Similarity	NPC90121
0.7872	Intermediate Similarity	NPC476488
0.7872	Intermediate Similarity	NPC474490
0.7865	Intermediate Similarity	NPC11804
0.7865	Intermediate Similarity	NPC65661
0.7865	Intermediate Similarity	NPC215364
0.7865	Intermediate Similarity	NPC86316
0.7865	Intermediate Similarity	NPC106416
0.7857	Intermediate Similarity	NPC16279
0.7857	Intermediate Similarity	NPC256640
0.7857	Intermediate Similarity	NPC235906
0.7857	Intermediate Similarity	NPC205615
0.7857	Intermediate Similarity	NPC475873
0.7849	Intermediate Similarity	NPC125674
0.7849	Intermediate Similarity	NPC475838
0.7849	Intermediate Similarity	NPC228451
0.7849	Intermediate Similarity	NPC139692
0.7841	Intermediate Similarity	NPC250315
0.7841	Intermediate Similarity	NPC193198
0.7841	Intermediate Similarity	NPC59097
0.7835	Intermediate Similarity	NPC47880
0.7835	Intermediate Similarity	NPC201718
0.7835	Intermediate Similarity	NPC469851
0.7831	Intermediate Similarity	NPC140287
0.7826	Intermediate Similarity	NPC469368
0.7826	Intermediate Similarity	NPC179394
0.7826	Intermediate Similarity	NPC476004
0.7826	Intermediate Similarity	NPC316228
0.7826	Intermediate Similarity	NPC474761
0.7826	Intermediate Similarity	NPC475855
0.7826	Intermediate Similarity	NPC144133
0.7822	Intermediate Similarity	NPC38154
0.7816	Intermediate Similarity	NPC141810
0.7816	Intermediate Similarity	NPC24417
0.7812	Intermediate Similarity	NPC471144
0.7812	Intermediate Similarity	NPC316598
0.7805	Intermediate Similarity	NPC163003
0.7802	Intermediate Similarity	NPC477302
0.7802	Intermediate Similarity	NPC260343
0.7802	Intermediate Similarity	NPC202672
0.78	Intermediate Similarity	NPC469853

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 NPC261721 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	186
0.1-0.2	1768
0.2-0.3	3632
0.3-0.4	2293
0.4-0.5	854
0.5-0.6	307
0.6-0.7	93
0.7-0.8	17
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
0.8022	Intermediate Similarity	NPD5785	Approved
0.7872	Intermediate Similarity	NPD1698	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD5363	Approved
0.7582	Intermediate Similarity	NPD5786	Approved
0.7528	Intermediate Similarity	NPD4269	Approved
0.7528	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD4270	Approved
0.7451	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7447	Intermediate Similarity	NPD6698	Approved
0.7447	Intermediate Similarity	NPD46	Approved
0.7444	Intermediate Similarity	NPD7154	Phase 3
0.7416	Intermediate Similarity	NPD5369	Approved
0.7333	Intermediate Similarity	NPD5209	Approved
0.7303	Intermediate Similarity	NPD4252	Approved
0.7273	Intermediate Similarity	NPD4225	Approved
0.7253	Intermediate Similarity	NPD5362	Discontinued
0.7238	Intermediate Similarity	NPD6371	Approved
0.7159	Intermediate Similarity	NPD4756	Discovery
0.7113	Intermediate Similarity	NPD5778	Approved
0.7113	Intermediate Similarity	NPD5779	Approved
0.7097	Intermediate Similarity	NPD1694	Approved
0.7083	Intermediate Similarity	NPD7838	Discovery
0.7079	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD5282	Discontinued
0.701	Intermediate Similarity	NPD7983	Approved
0.6979	Remote Similarity	NPD6101	Approved
0.6979	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6435	Approved
0.6923	Remote Similarity	NPD5790	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD6082	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD6686	Approved
0.6867	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD7115	Discovery
0.6837	Remote Similarity	NPD6411	Approved
0.6832	Remote Similarity	NPD6084	Phase 2
0.6832	Remote Similarity	NPD6083	Phase 2
0.6809	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD5370	Suspended
0.68	Remote Similarity	NPD5695	Phase 3
0.6774	Remote Similarity	NPD4800	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD6399	Phase 3
0.6765	Remote Similarity	NPD7638	Approved
0.6765	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD4822	Approved
0.6739	Remote Similarity	NPD5368	Approved
0.6739	Remote Similarity	NPD4819	Approved
0.6739	Remote Similarity	NPD4821	Approved
0.6739	Remote Similarity	NPD4695	Discontinued
0.6739	Remote Similarity	NPD4820	Approved
0.6737	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6733	Remote Similarity	NPD7839	Suspended
0.6703	Remote Similarity	NPD4268	Approved
0.6703	Remote Similarity	NPD4271	Approved
0.6702	Remote Similarity	NPD5331	Approved
0.6702	Remote Similarity	NPD5332	Approved
0.6701	Remote Similarity	NPD5737	Approved
0.6701	Remote Similarity	NPD6672	Approved
0.6699	Remote Similarity	NPD7640	Approved
0.6699	Remote Similarity	NPD7639	Approved
0.6667	Remote Similarity	NPD5279	Phase 3
0.6667	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD4790	Discontinued
0.6667	Remote Similarity	NPD5693	Phase 1
0.6636	Remote Similarity	NPD5697	Approved
0.6633	Remote Similarity	NPD1695	Approved
0.6627	Remote Similarity	NPD2664	Clinical (unspecified phase)
0.6602	Remote Similarity	NPD5696	Approved
0.6588	Remote Similarity	NPD3704	Approved
0.6574	Remote Similarity	NPD6899	Approved
0.6574	Remote Similarity	NPD6011	Approved
0.6574	Remote Similarity	NPD6881	Approved
0.6556	Remote Similarity	NPD8039	Approved
0.6548	Remote Similarity	NPD3197	Phase 1
0.6545	Remote Similarity	NPD6650	Approved
0.6545	Remote Similarity	NPD6649	Approved
0.6545	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6542	Remote Similarity	NPD6402	Approved
0.6542	Remote Similarity	NPD5739	Approved
0.6542	Remote Similarity	NPD6675	Approved
0.6542	Remote Similarity	NPD7128	Approved
0.6535	Remote Similarity	NPD7748	Approved
0.6514	Remote Similarity	NPD6373	Approved
0.6514	Remote Similarity	NPD6014	Approved
0.6514	Remote Similarity	NPD6013	Approved
0.6514	Remote Similarity	NPD6372	Approved
0.6514	Remote Similarity	NPD6012	Approved
0.6505	Remote Similarity	NPD7902	Approved
0.65	Remote Similarity	NPD7637	Suspended
0.65	Remote Similarity	NPD7515	Phase 2
0.6495	Remote Similarity	NPD7521	Approved
0.6495	Remote Similarity	NPD7334	Approved
0.6495	Remote Similarity	NPD5330	Approved
0.6495	Remote Similarity	NPD7146	Approved
0.6495	Remote Similarity	NPD6684	Approved
0.6495	Remote Similarity	NPD6409	Approved
0.6495	Remote Similarity	NPD4249	Approved
0.6486	Remote Similarity	NPD6053	Discontinued
0.6481	Remote Similarity	NPD5701	Approved
0.6465	Remote Similarity	NPD4753	Phase 2
0.6458	Remote Similarity	NPD3666	Approved
0.6458	Remote Similarity	NPD3665	Phase 1
0.6458	Remote Similarity	NPD3133	Approved
0.6455	Remote Similarity	NPD7290	Approved
0.6455	Remote Similarity	NPD7102	Approved
0.6455	Remote Similarity	NPD6883	Approved
0.6429	Remote Similarity	NPD4250	Approved
0.6429	Remote Similarity	NPD4251	Approved
0.6422	Remote Similarity	NPD7320	Approved
0.6421	Remote Similarity	NPD3667	Approved
0.6408	Remote Similarity	NPD5222	Approved
0.6408	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6408	Remote Similarity	NPD4697	Phase 3
0.6408	Remote Similarity	NPD5221	Approved
0.6396	Remote Similarity	NPD6617	Approved
0.6396	Remote Similarity	NPD8130	Phase 1
0.6396	Remote Similarity	NPD6847	Approved
0.6396	Remote Similarity	NPD6869	Approved
0.6395	Remote Similarity	NPD7331	Phase 2
0.6383	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6903	Approved
0.6364	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6346	Remote Similarity	NPD5173	Approved
0.6339	Remote Similarity	NPD6882	Approved
0.6339	Remote Similarity	NPD8297	Approved
0.6327	Remote Similarity	NPD3618	Phase 1
0.6321	Remote Similarity	NPD5344	Discontinued
0.6311	Remote Similarity	NPD4629	Approved
0.6311	Remote Similarity	NPD5210	Approved
0.63	Remote Similarity	NPD6080	Approved
0.63	Remote Similarity	NPD6673	Approved
0.63	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.63	Remote Similarity	NPD6904	Approved
0.6289	Remote Similarity	NPD4786	Approved
0.6279	Remote Similarity	NPD7341	Phase 2
0.6262	Remote Similarity	NPD5211	Phase 2
0.625	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6319	Approved
0.6238	Remote Similarity	NPD5692	Phase 3
0.6226	Remote Similarity	NPD5286	Approved
0.6226	Remote Similarity	NPD4696	Approved
0.6226	Remote Similarity	NPD5285	Approved
0.6224	Remote Similarity	NPD1696	Phase 3
0.6216	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD7900	Approved
0.6214	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6207	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6204	Remote Similarity	NPD6647	Phase 2
0.619	Remote Similarity	NPD4755	Approved
0.6186	Remote Similarity	NPD6110	Phase 1
0.6176	Remote Similarity	NPD6079	Approved
0.6176	Remote Similarity	NPD6050	Approved
0.6176	Remote Similarity	NPD5694	Approved
0.6174	Remote Similarity	NPD6868	Approved
0.6174	Remote Similarity	NPD6274	Approved
0.6168	Remote Similarity	NPD5223	Approved
0.6162	Remote Similarity	NPD6422	Discontinued
0.6162	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD5690	Phase 2
0.6161	Remote Similarity	NPD2067	Discontinued
0.6161	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6147	Remote Similarity	NPD5141	Approved
0.614	Remote Similarity	NPD4632	Approved
0.6139	Remote Similarity	NPD5328	Approved
0.6122	Remote Similarity	NPD4197	Approved
0.6121	Remote Similarity	NPD6317	Approved
0.6111	Remote Similarity	NPD5224	Approved
0.6111	Remote Similarity	NPD7632	Discontinued
0.6111	Remote Similarity	NPD5226	Approved
0.6111	Remote Similarity	NPD4633	Approved
0.6111	Remote Similarity	NPD5225	Approved
0.6106	Remote Similarity	NPD7116	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6075	Remote Similarity	NPD4700	Approved
0.6075	Remote Similarity	NPD6648	Approved
0.6068	Remote Similarity	NPD6314	Approved
0.6068	Remote Similarity	NPD6313	Approved
0.6068	Remote Similarity	NPD6335	Approved
0.6061	Remote Similarity	NPD5329	Approved
0.6055	Remote Similarity	NPD5175	Approved
0.6055	Remote Similarity	NPD5174	Approved
0.6033	Remote Similarity	NPD7492	Approved
0.6019	Remote Similarity	NPD5284	Approved
0.6019	Remote Similarity	NPD5281	Approved
0.6018	Remote Similarity	NPD4634	Approved
0.6017	Remote Similarity	NPD7100	Approved
0.6017	Remote Similarity	NPD7101	Approved
0.6016	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3732	Approved
0.6	Remote Similarity	NPD4519	Discontinued
0.6	Remote Similarity	NPD1376	Discontinued
0.6	Remote Similarity	NPD4694	Approved
0.6	Remote Similarity	NPD4246	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5280	Approved
0.6	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD4623	Approved
0.6	Remote Similarity	NPD6098	Approved
0.6	Remote Similarity	NPD3617	Approved
0.5984	Remote Similarity	NPD6616	Approved
0.5983	Remote Similarity	NPD6009	Approved
0.5983	Remote Similarity	NPD7500	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