NPASS Compound

Structure

NPC476336 OpenBabel07101719132D 26 29 0 0 1 0 0 0 0 0999 V2000 4.1653 2.0637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1971 -2.2562 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6617 -0.4452 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2052 1.9628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0487 -1.3023 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8125 1.0809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8812 2.6089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7173 3.0915 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1484 -0.9539 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7173 1.1608 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6578 0.2247 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0389 2.1262 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9443 0.2007 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8812 1.6435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8923 0.8791 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5533 2.6089 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5533 1.6435 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0452 1.1608 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1633 1.5535 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5269 1.4705 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4827 0.8360 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0466 2.2840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4428 0.9369 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4714 2.9072 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4714 1.3452 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 2 5 2 0 0 0 0 3 13 1 0 0 0 0 4 6 1 0 0 0 0 5 9 1 0 0 0 0 6 15 1 0 0 0 0 7 8 2 0 0 0 0 7 14 1 0 0 0 0 8 16 1 0 0 0 0 10 14 2 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 22 1 0 0 0 0 12 25 1 0 0 0 0 12 26 1 0 0 0 0 13 18 1 0 0 0 0 13 22 1 6 0 0 0 15 20 1 0 0 0 0 16 17 2 0 0 0 0 16 25 1 0 0 0 0 17 26 1 0 0 0 0 18 14 1 1 0 0 0 18 19 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 23 2 0 0 0 0 21 22 1 6 0 0 0 21 24 1 0 0 0 0 22 9 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	352.17
Volume:	371.548
LogP:	3.25
LogD:	3.165
LogS:	-4.453
# Rotatable Bonds:	5
TPSA:	55.76
# H-Bond Aceptor:	4
# H-Bond Donor:	1
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.82
Synthetic Accessibility Score:	5.246
Fsp3:	0.409
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:	-4.522
MDCK Permeability:	1.742928543535527e-05
Pgp-inhibitor:	0.99
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.004
20% Bioavailability (F20%):	0.178
30% Bioavailability (F30%):	0.71

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.18
Plasma Protein Binding (PPB):	91.61958312988281%
Volume Distribution (VD):	0.815
Pgp-substrate:	3.5863523483276367%

ADMET: Metabolism

CYP1A2-inhibitor:	0.711
CYP1A2-substrate:	0.254
CYP2C19-inhibitor:	0.866
CYP2C19-substrate:	0.501
CYP2C9-inhibitor:	0.614
CYP2C9-substrate:	0.717
CYP2D6-inhibitor:	0.964
CYP2D6-substrate:	0.796
CYP3A4-inhibitor:	0.963
CYP3A4-substrate:	0.382

ADMET: Excretion

Clearance (CL):	14.388
Half-life (T1/2):	0.406

ADMET: Toxicity

hERG Blockers:	0.304
Human Hepatotoxicity (H-HT):	0.074
Drug-inuced Liver Injury (DILI):	0.039
AMES Toxicity:	0.022
Rat Oral Acute Toxicity:	0.578
Maximum Recommended Daily Dose:	0.913
Skin Sensitization:	0.919
Carcinogencity:	0.447
Eye Corrosion:	0.004
Eye Irritation:	0.024
Respiratory Toxicity:	0.92

Download Data

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

Natural Product: NPC476336

Natural Product ID:	NPC476336
*Common Name:**	2'-Epi-Guianin
IUPAC Name:	(5R,6R,7R,8S)-7-(1,3-benzodioxol-5-yl)-8-hydroxy-6-methyl-3,5-bis(prop-2-enyl)bicyclo[3.2.1]oct-3-en-2-one
Synonyms:	2'-Epi-Guianin
Standard InCHIKey:	IELYWLBCFOCUNW-KUXMWZRESA-N
Standard InCHI:	InChI=1S/C22H24O4/c1-4-6-15-11-22(9-5-2)13(3)18(19(20(15)23)21(22)24)14-7-8-16-17(10-14)26-12-25-16/h4-5,7-8,10-11,13,18-19,21,24H,1-2,6,9,12H2,3H3/t13-,18+,19?,21+,22+/m1/s1
SMILES:	C=CC[C@@]12C=C(CC=C)C(=O)C([C@@H]1O)[C@@H]([C@H]2C)c1ccc2c(c1)OCO2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL570978
PubChem CID:	45487149
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000296] Benzodioxoles

*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
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19548690]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO27964	Nectandra amazonum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO19526	Pleurothyrium cinereum	Species	Lauraceae	Eukaryota	leaves	n.a.	n.a.	PMID[19880317]
NPO26326	Ocotea macrophylla	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27964	Nectandra amazonum	Species	Lauraceae	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	6
Others	1

Activity Type	# Activity
Individual Protein	2
NON-MOLECULAR	3
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT324	Individual Protein	Cyclooxygenase-1	Ovis aries	IC50	=	18200.0	nM	PMID[468882]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	326000.0	nM	PMID[468882]
NPT2	Others	Unspecified		IC50	=	113000.0	nM	PMID[468882]
NPT2	Others	Unspecified		Ratio IC50	=	0.0558	n.a.	PMID[468882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	1610.0	nM	PMID[468882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	2620.0	nM	PMID[468882]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	23100.0	nM	PMID[468882]

☑ 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 NPC476336 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	318
0.1-0.2	1268
0.2-0.3	2634
0.3-0.4	6232
0.4-0.5	12274
0.5-0.6	6159
0.6-0.7	12114
0.7-0.8	1630
0.8-0.85	51
0.85-0.9	13
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9257	High Similarity	NPC476364
0.8986	High Similarity	NPC12854
0.8954	High Similarity	NPC476337
0.8897	High Similarity	NPC472564
0.8784	High Similarity	NPC476338
0.8784	High Similarity	NPC476359
0.8716	High Similarity	NPC189054
0.8675	High Similarity	NPC178048
0.8671	High Similarity	NPC476277
0.8645	High Similarity	NPC475095
0.8582	High Similarity	NPC477694
0.8582	High Similarity	NPC477705
0.8581	High Similarity	NPC15743
0.8571	High Similarity	NPC104956
0.8552	High Similarity	NPC231719
0.8552	High Similarity	NPC52968
0.8543	High Similarity	NPC472567
0.8523	High Similarity	NPC327052
0.8521	High Similarity	NPC477706
0.8503	High Similarity	NPC51681
0.8503	High Similarity	NPC323601
0.85	High Similarity	NPC64948
0.8497	Intermediate Similarity	NPC476335
0.8481	Intermediate Similarity	NPC476244
0.8435	Intermediate Similarity	NPC470855
0.8431	Intermediate Similarity	NPC163002
0.8408	Intermediate Similarity	NPC472565
0.8378	Intermediate Similarity	NPC28398
0.8367	Intermediate Similarity	NPC178290
0.8345	Intermediate Similarity	NPC244876
0.8344	Intermediate Similarity	NPC472560
0.8299	Intermediate Similarity	NPC166184
0.8289	Intermediate Similarity	NPC25496
0.8276	Intermediate Similarity	NPC327410
0.8243	Intermediate Similarity	NPC318575
0.8228	Intermediate Similarity	NPC476340
0.8217	Intermediate Similarity	NPC476363
0.8212	Intermediate Similarity	NPC46880
0.8188	Intermediate Similarity	NPC278076
0.8176	Intermediate Similarity	NPC179914
0.8151	Intermediate Similarity	NPC205915
0.8143	Intermediate Similarity	NPC256167
0.8141	Intermediate Similarity	NPC28724
0.8133	Intermediate Similarity	NPC166137
0.8133	Intermediate Similarity	NPC282291
0.8129	Intermediate Similarity	NPC475170
0.8112	Intermediate Similarity	NPC20404
0.8112	Intermediate Similarity	NPC293641
0.8112	Intermediate Similarity	NPC12022
0.8112	Intermediate Similarity	NPC20287
0.8108	Intermediate Similarity	NPC102260
0.8108	Intermediate Similarity	NPC230968
0.8105	Intermediate Similarity	NPC30890
0.8095	Intermediate Similarity	NPC37065
0.8082	Intermediate Similarity	NPC239302
0.8079	Intermediate Similarity	NPC52664
0.8072	Intermediate Similarity	NPC475197
0.8072	Intermediate Similarity	NPC473467
0.8069	Intermediate Similarity	NPC137427
0.8069	Intermediate Similarity	NPC215941
0.8069	Intermediate Similarity	NPC275724
0.8069	Intermediate Similarity	NPC311419
0.8069	Intermediate Similarity	NPC244246
0.8069	Intermediate Similarity	NPC65935
0.8069	Intermediate Similarity	NPC319282
0.8069	Intermediate Similarity	NPC123196
0.8056	Intermediate Similarity	NPC278308
0.8052	Intermediate Similarity	NPC153620
0.8052	Intermediate Similarity	NPC24257
0.8042	Intermediate Similarity	NPC213711
0.8042	Intermediate Similarity	NPC40352
0.8026	Intermediate Similarity	NPC86455
0.8026	Intermediate Similarity	NPC125134
0.8026	Intermediate Similarity	NPC137920
0.8025	Intermediate Similarity	NPC56184
0.8012	Intermediate Similarity	NPC96194
0.8012	Intermediate Similarity	NPC299855
0.8012	Intermediate Similarity	NPC239818
0.8012	Intermediate Similarity	NPC218471
0.7987	Intermediate Similarity	NPC90431
0.7987	Intermediate Similarity	NPC3982
0.7975	Intermediate Similarity	NPC105942
0.7975	Intermediate Similarity	NPC308555
0.7975	Intermediate Similarity	NPC205392
0.7974	Intermediate Similarity	NPC50696
0.7973	Intermediate Similarity	NPC19890
0.7973	Intermediate Similarity	NPC110958
0.7965	Intermediate Similarity	NPC189704
0.7962	Intermediate Similarity	NPC475311
0.7962	Intermediate Similarity	NPC473680
0.7962	Intermediate Similarity	NPC475454
0.7962	Intermediate Similarity	NPC473579
0.7959	Intermediate Similarity	NPC104077
0.7959	Intermediate Similarity	NPC147616
0.7959	Intermediate Similarity	NPC259742
0.7959	Intermediate Similarity	NPC219671
0.795	Intermediate Similarity	NPC76211
0.795	Intermediate Similarity	NPC68619
0.7949	Intermediate Similarity	NPC477698
0.7947	Intermediate Similarity	NPC322021
0.7947	Intermediate Similarity	NPC474784
0.7945	Intermediate Similarity	NPC172673
0.7945	Intermediate Similarity	NPC280399
0.7945	Intermediate Similarity	NPC233961
0.7945	Intermediate Similarity	NPC195292
0.7945	Intermediate Similarity	NPC339621
0.7922	Intermediate Similarity	NPC280717
0.7922	Intermediate Similarity	NPC271607
0.7919	Intermediate Similarity	NPC476067
0.7919	Intermediate Similarity	NPC475121
0.7919	Intermediate Similarity	NPC252343
0.7919	Intermediate Similarity	NPC174191
0.7917	Intermediate Similarity	NPC475244
0.7901	Intermediate Similarity	NPC474936
0.7898	Intermediate Similarity	NPC177830
0.7895	Intermediate Similarity	NPC82336
0.7895	Intermediate Similarity	NPC78987
0.7888	Intermediate Similarity	NPC286919
0.7888	Intermediate Similarity	NPC475663
0.7885	Intermediate Similarity	NPC308178
0.7877	Intermediate Similarity	NPC304622
0.7875	Intermediate Similarity	NPC186316
0.7875	Intermediate Similarity	NPC254163
0.7871	Intermediate Similarity	NPC476362
0.7866	Intermediate Similarity	NPC100420
0.7862	Intermediate Similarity	NPC276466
0.7862	Intermediate Similarity	NPC5018
0.7862	Intermediate Similarity	NPC151167
0.7862	Intermediate Similarity	NPC286683
0.7862	Intermediate Similarity	NPC123722
0.7862	Intermediate Similarity	NPC123228
0.7862	Intermediate Similarity	NPC223807
0.7857	Intermediate Similarity	NPC474036
0.7857	Intermediate Similarity	NPC239608
0.7857	Intermediate Similarity	NPC46161
0.7852	Intermediate Similarity	NPC5310
0.7852	Intermediate Similarity	NPC300776
0.7852	Intermediate Similarity	NPC4982
0.7852	Intermediate Similarity	NPC68779
0.7852	Intermediate Similarity	NPC471110
0.7852	Intermediate Similarity	NPC176814
0.7848	Intermediate Similarity	NPC118033
0.7848	Intermediate Similarity	NPC62354
0.7848	Intermediate Similarity	NPC475379
0.7848	Intermediate Similarity	NPC164082
0.7847	Intermediate Similarity	NPC85830
0.7843	Intermediate Similarity	NPC476842
0.7843	Intermediate Similarity	NPC476840
0.7843	Intermediate Similarity	NPC472410
0.7843	Intermediate Similarity	NPC46180
0.784	Intermediate Similarity	NPC469384
0.7838	Intermediate Similarity	NPC106739
0.7834	Intermediate Similarity	NPC161955
0.7832	Intermediate Similarity	NPC4181
0.7832	Intermediate Similarity	NPC257976
0.7832	Intermediate Similarity	NPC249788
0.7832	Intermediate Similarity	NPC242372
0.7832	Intermediate Similarity	NPC164778
0.7826	Intermediate Similarity	NPC478055
0.7823	Intermediate Similarity	NPC171550
0.7823	Intermediate Similarity	NPC142985
0.7823	Intermediate Similarity	NPC134764
0.7821	Intermediate Similarity	NPC88345
0.7818	Intermediate Similarity	NPC474301
0.7817	Intermediate Similarity	NPC114845
0.7817	Intermediate Similarity	NPC301641
0.7817	Intermediate Similarity	NPC80241
0.7815	Intermediate Similarity	NPC14022
0.7812	Intermediate Similarity	NPC136757
0.7806	Intermediate Similarity	NPC235195
0.7806	Intermediate Similarity	NPC19862
0.7806	Intermediate Similarity	NPC223185
0.7805	Intermediate Similarity	NPC206815
0.7805	Intermediate Similarity	NPC476011
0.7801	Intermediate Similarity	NPC344161
0.78	Intermediate Similarity	NPC470990
0.7799	Intermediate Similarity	NPC475579
0.7799	Intermediate Similarity	NPC473773
0.7799	Intermediate Similarity	NPC151425
0.7793	Intermediate Similarity	NPC274356
0.7793	Intermediate Similarity	NPC90128
0.7793	Intermediate Similarity	NPC84076
0.7793	Intermediate Similarity	NPC303680
0.7793	Intermediate Similarity	NPC179777
0.7792	Intermediate Similarity	NPC474966
0.7785	Intermediate Similarity	NPC37220
0.7785	Intermediate Similarity	NPC147224
0.7785	Intermediate Similarity	NPC158635
0.7785	Intermediate Similarity	NPC237441
0.7785	Intermediate Similarity	NPC229882
0.7785	Intermediate Similarity	NPC169973
0.7784	Intermediate Similarity	NPC475299
0.7784	Intermediate Similarity	NPC21956
0.7778	Intermediate Similarity	NPC246474
0.7778	Intermediate Similarity	NPC100675
0.7778	Intermediate Similarity	NPC273686
0.7778	Intermediate Similarity	NPC162851
0.7778	Intermediate Similarity	NPC312404
0.7778	Intermediate Similarity	NPC218092
0.7771	Intermediate Similarity	NPC230670

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 NPC476336 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	276
0.1-0.2	850
0.2-0.3	1603
0.3-0.4	2576
0.4-0.5	2188
0.5-0.6	1188
0.6-0.7	424
0.7-0.8	44
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8926	High Similarity	NPD7028	Phase 2
0.7857	Intermediate Similarity	NPD1357	Approved
0.7843	Intermediate Similarity	NPD4110	Phase 3
0.7843	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD8127	Discontinued
0.7718	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7718	Intermediate Similarity	NPD3620	Phase 2
0.7707	Intermediate Similarity	NPD6273	Approved
0.764	Intermediate Similarity	NPD37	Approved
0.7636	Intermediate Similarity	NPD7199	Phase 2
0.7607	Intermediate Similarity	NPD4967	Phase 2
0.7607	Intermediate Similarity	NPD4965	Approved
0.7607	Intermediate Similarity	NPD4966	Approved
0.7551	Intermediate Similarity	NPD5647	Approved
0.7483	Intermediate Similarity	NPD4140	Approved
0.7466	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD5536	Phase 2
0.7453	Intermediate Similarity	NPD7458	Discontinued
0.7442	Intermediate Similarity	NPD7685	Pre-registration
0.744	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD3818	Discontinued
0.741	Intermediate Similarity	NPD6234	Discontinued
0.7389	Intermediate Similarity	NPD8166	Discontinued
0.7371	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7329	Intermediate Similarity	NPD3705	Approved
0.732	Intermediate Similarity	NPD5735	Approved
0.732	Intermediate Similarity	NPD6355	Discontinued
0.732	Intermediate Similarity	NPD3657	Discovery
0.7315	Intermediate Similarity	NPD2798	Approved
0.7305	Intermediate Similarity	NPD5283	Phase 1
0.7303	Intermediate Similarity	NPD6663	Approved
0.7297	Intermediate Similarity	NPD1876	Approved
0.7278	Intermediate Similarity	NPD4628	Phase 3
0.7273	Intermediate Similarity	NPD6653	Approved
0.7209	Intermediate Similarity	NPD7228	Approved
0.72	Intermediate Similarity	NPD4624	Approved
0.7197	Intermediate Similarity	NPD6004	Phase 3
0.7197	Intermediate Similarity	NPD5762	Approved
0.7197	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7197	Intermediate Similarity	NPD6002	Phase 3
0.7197	Intermediate Similarity	NPD6005	Phase 3
0.7197	Intermediate Similarity	NPD5763	Approved
0.7197	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD2932	Approved
0.719	Intermediate Similarity	NPD8032	Phase 2
0.7179	Intermediate Similarity	NPD2799	Discontinued
0.7161	Intermediate Similarity	NPD6353	Approved
0.716	Intermediate Similarity	NPD5494	Approved
0.7152	Intermediate Similarity	NPD9494	Approved
0.7152	Intermediate Similarity	NPD5736	Approved
0.7134	Intermediate Similarity	NPD2935	Discontinued
0.7126	Intermediate Similarity	NPD7074	Phase 3
0.7114	Intermediate Similarity	NPD5327	Phase 3
0.7083	Intermediate Similarity	NPD3882	Suspended
0.7075	Intermediate Similarity	NPD3019	Approved
0.7069	Intermediate Similarity	NPD7054	Approved
0.7067	Intermediate Similarity	NPD1283	Approved
0.7063	Intermediate Similarity	NPD1241	Discontinued
0.7048	Intermediate Similarity	NPD6873	Phase 2
0.7047	Intermediate Similarity	NPD3972	Approved
0.7045	Intermediate Similarity	NPD7240	Approved
0.7045	Intermediate Similarity	NPD6765	Approved
0.7045	Intermediate Similarity	NPD6764	Approved
0.7045	Intermediate Similarity	NPD6559	Discontinued
0.7029	Intermediate Similarity	NPD7472	Approved
0.7011	Intermediate Similarity	NPD7799	Discontinued
0.7007	Intermediate Similarity	NPD1651	Approved
0.7006	Intermediate Similarity	NPD1934	Approved
0.6987	Remote Similarity	NPD447	Suspended
0.6987	Remote Similarity	NPD1933	Approved
0.6966	Remote Similarity	NPD7157	Approved
0.6964	Remote Similarity	NPD2393	Clinical (unspecified phase)
0.6964	Remote Similarity	NPD5760	Phase 2
0.6964	Remote Similarity	NPD5761	Phase 2
0.6961	Remote Similarity	NPD8397	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3095	Discontinued
0.6948	Remote Similarity	NPD3027	Phase 3
0.6948	Remote Similarity	NPD7095	Approved
0.6941	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6939	Remote Similarity	NPD3091	Approved
0.6923	Remote Similarity	NPD228	Approved
0.6923	Remote Similarity	NPD5977	Approved
0.6923	Remote Similarity	NPD5978	Approved
0.6918	Remote Similarity	NPD2438	Suspended
0.6918	Remote Similarity	NPD5712	Approved
0.6913	Remote Similarity	NPD3026	Approved
0.6913	Remote Similarity	NPD3023	Approved
0.691	Remote Similarity	NPD7808	Phase 3
0.6908	Remote Similarity	NPD6362	Approved
0.6903	Remote Similarity	NPD6798	Discontinued
0.6894	Remote Similarity	NPD6674	Discontinued
0.6893	Remote Similarity	NPD6797	Phase 2
0.6892	Remote Similarity	NPD3024	Approved
0.6892	Remote Similarity	NPD3025	Approved
0.6889	Remote Similarity	NPD6785	Approved
0.6889	Remote Similarity	NPD6784	Approved
0.6879	Remote Similarity	NPD7315	Approved
0.6875	Remote Similarity	NPD7266	Discontinued
0.6871	Remote Similarity	NPD7236	Approved
0.6867	Remote Similarity	NPD3092	Approved
0.6867	Remote Similarity	NPD1281	Approved
0.6864	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7473	Discontinued
0.6854	Remote Similarity	NPD7251	Discontinued
0.6852	Remote Similarity	NPD7003	Approved
0.6852	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6846	Remote Similarity	NPD4626	Approved
0.6839	Remote Similarity	NPD5952	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD2492	Phase 1
0.6832	Remote Similarity	NPD4534	Discontinued
0.6832	Remote Similarity	NPD5958	Discontinued
0.6832	Remote Similarity	NPD2424	Discontinued
0.6824	Remote Similarity	NPD3817	Phase 2
0.6816	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6815	Remote Similarity	NPD2979	Phase 3
0.6815	Remote Similarity	NPD4060	Phase 1
0.6813	Remote Similarity	NPD2161	Phase 2
0.6802	Remote Similarity	NPD919	Approved
0.68	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.68	Remote Similarity	NPD6166	Phase 2
0.6797	Remote Similarity	NPD3094	Phase 2
0.6792	Remote Similarity	NPD7097	Phase 1
0.6788	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD6599	Discontinued
0.6786	Remote Similarity	NPD4380	Phase 2
0.6782	Remote Similarity	NPD6232	Discontinued
0.678	Remote Similarity	NPD5844	Phase 1
0.6779	Remote Similarity	NPD5585	Approved
0.6779	Remote Similarity	NPD5691	Approved
0.677	Remote Similarity	NPD2344	Approved
0.677	Remote Similarity	NPD2346	Discontinued
0.677	Remote Similarity	NPD2343	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD1653	Approved
0.6765	Remote Similarity	NPD7819	Suspended
0.6765	Remote Similarity	NPD2801	Approved
0.6765	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6761	Remote Similarity	NPD1358	Approved
0.6758	Remote Similarity	NPD8434	Phase 2
0.6753	Remote Similarity	NPD5740	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6007	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD6085	Phase 2
0.6752	Remote Similarity	NPD4062	Phase 3
0.6752	Remote Similarity	NPD6233	Phase 2
0.6748	Remote Similarity	NPD6331	Phase 2
0.674	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6723	Remote Similarity	NPD3751	Discontinued
0.6713	Remote Similarity	NPD2684	Approved
0.6711	Remote Similarity	NPD1608	Approved
0.6707	Remote Similarity	NPD5699	Approved
0.6707	Remote Similarity	NPD5084	Clinical (unspecified phase)
0.6705	Remote Similarity	NPD2898	Approved
0.669	Remote Similarity	NPD3134	Approved
0.6689	Remote Similarity	NPD3847	Discontinued
0.6688	Remote Similarity	NPD3268	Approved
0.6688	Remote Similarity	NPD2313	Discontinued
0.6688	Remote Similarity	NPD2797	Approved
0.6687	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD8312	Approved
0.6685	Remote Similarity	NPD7280	Phase 3
0.6685	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6685	Remote Similarity	NPD7281	Phase 3
0.6685	Remote Similarity	NPD8313	Approved
0.6667	Remote Similarity	NPD8455	Phase 2
0.6667	Remote Similarity	NPD7239	Suspended
0.6648	Remote Similarity	NPD3926	Phase 2
0.6647	Remote Similarity	NPD7075	Discontinued
0.6646	Remote Similarity	NPD7033	Discontinued
0.6646	Remote Similarity	NPD1510	Phase 2
0.6646	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD7843	Approved
0.6629	Remote Similarity	NPD1247	Approved
0.6627	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD3866	Clinical (unspecified phase)
0.6627	Remote Similarity	NPD6799	Approved
0.6626	Remote Similarity	NPD970	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD2157	Approved
0.6623	Remote Similarity	NPD8651	Approved
0.6623	Remote Similarity	NPD1778	Approved
0.6613	Remote Similarity	NPD7296	Approved
0.6609	Remote Similarity	NPD6315	Phase 2
0.6608	Remote Similarity	NPD6801	Discontinued
0.6606	Remote Similarity	NPD6190	Approved
0.6606	Remote Similarity	NPD2309	Approved
0.6606	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD2796	Approved
0.6605	Remote Similarity	NPD2531	Phase 2
0.6604	Remote Similarity	NPD1240	Approved
0.6603	Remote Similarity	NPD2861	Phase 2
0.66	Remote Similarity	NPD1894	Discontinued
0.6591	Remote Similarity	NPD3787	Discontinued
0.659	Remote Similarity	NPD4868	Clinical (unspecified phase)
0.6587	Remote Similarity	NPD2533	Approved
0.6587	Remote Similarity	NPD2534	Approved
0.6587	Remote Similarity	NPD2532	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