NPASS Compound

Structure

NPC476362 OpenBabel07101719152D 28 30 0 0 1 0 0 0 0 0999 V2000 2.9909 -0.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6637 -0.4458 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 4.5451 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.2317 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3946 4.0618 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6042 -1.5612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3840 0.3003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8159 1.0822 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8835 2.6120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 1.1622 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6586 0.2250 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9454 0.2010 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8934 0.8802 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8835 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 3.0953 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 1.6455 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0464 1.1622 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1635 1.5553 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 0.5275 1.4722 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5576 2.6120 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4833 0.8370 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0479 2.2867 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4445 0.9381 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.7205 4.0618 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3946 1.1622 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3946 3.0953 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1486 -0.9550 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 2 0 0 0 0 2 12 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 27 1 0 0 0 0 6 28 1 0 0 0 0 7 8 1 0 0 0 0 8 13 1 0 0 0 0 9 14 2 0 0 0 0 9 15 1 0 0 0 0 10 14 1 0 0 0 0 10 16 2 0 0 0 0 11 13 2 0 0 0 0 11 22 1 0 0 0 0 12 17 1 0 0 0 0 12 22 1 6 0 0 0 13 19 1 0 0 0 0 15 20 2 0 0 0 0 15 25 1 0 0 0 0 16 20 1 0 0 0 0 16 26 1 0 0 0 0 17 14 1 1 0 0 0 17 18 1 0 0 0 0 18 19 1 0 0 0 0 18 21 1 0 0 0 0 19 23 2 0 0 0 0 20 27 1 0 0 0 0 21 22 1 0 0 0 0 21 24 2 0 0 0 0 22 28 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	386.17
Volume:	397.685
LogP:	2.597
LogD:	2.409
LogS:	-4.249
# Rotatable Bonds:	7
TPSA:	71.06
# H-Bond Aceptor:	6
# H-Bond Donor:	0
# Rings:	3
# Heavy Atoms:	6

MedChem Properties

QED Drug-Likeness Score:	0.53
Synthetic Accessibility Score:	4.926
Fsp3:	0.455
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.52
MDCK Permeability:	1.5931833331706002e-05
Pgp-inhibitor:	0.998
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.021
20% Bioavailability (F20%):	0.013
30% Bioavailability (F30%):	0.476

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.301
Plasma Protein Binding (PPB):	79.95606231689453%
Volume Distribution (VD):	1.027
Pgp-substrate:	11.362676620483398%

ADMET: Metabolism

CYP1A2-inhibitor:	0.031
CYP1A2-substrate:	0.964
CYP2C19-inhibitor:	0.167
CYP2C19-substrate:	0.887
CYP2C9-inhibitor:	0.084
CYP2C9-substrate:	0.155
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.335
CYP3A4-inhibitor:	0.881
CYP3A4-substrate:	0.911

ADMET: Excretion

Clearance (CL):	10.093
Half-life (T1/2):	0.481

ADMET: Toxicity

hERG Blockers:	0.031
Human Hepatotoxicity (H-HT):	0.328
Drug-inuced Liver Injury (DILI):	0.06
AMES Toxicity:	0.017
Rat Oral Acute Toxicity:	0.832
Maximum Recommended Daily Dose:	0.66
Skin Sensitization:	0.087
Carcinogencity:	0.581
Eye Corrosion:	0.008
Eye Irritation:	0.027
Respiratory Toxicity:	0.973

Download Data

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

Natural Product: NPC476362

Natural Product ID:	NPC476362
*Common Name:**	4'-Oxo-Macrophyllin B
IUPAC Name:	(5S,6R,7R)-5-methoxy-6-methyl-3-prop-2-enyl-7-(3,4,5-trimethoxyphenyl)bicyclo[3.2.1]oct-3-ene-2,8-dione
Synonyms:
Standard InCHIKey:	FLIHMBQDBZWUAD-VQNGQWKISA-N
Standard InCHI:	InChI=1S/C22H26O6/c1-7-8-13-11-22(28-6)12(2)17(18(19(13)23)21(22)24)14-9-15(25-3)20(27-5)16(10-14)26-4/h7,9-12,17-18H,1,8H2,2-6H3/t12-,17+,18?,22-/m1/s1
SMILES:	CC1C(C2C(=O)C(=CC1(C2=O)OC)CC=C)C3=CC(=C(C(=C3)OC)OC)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL584539
PubChem CID:	45487143
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0002341] Phenol ethers [CHEMONTID:0000138] Anisoles

*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	=	356000.0	nM	PMID[515260]
NPT325	Individual Protein	Cyclooxygenase-2	Ovis aries	IC50	=	844000.0	nM	PMID[515260]
NPT2	Others	Unspecified		IC50	=	92500.0	nM	PMID[515260]
NPT2	Others	Unspecified		Ratio IC50	=	0.422	n.a.	PMID[515260]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	7470.0	nM	PMID[515260]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	78900.0	nM	PMID[515260]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	521000.0	nM	PMID[515260]

☑ 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 NPC476362 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	467
0.1-0.2	1591
0.2-0.3	3576
0.3-0.4	9385
0.4-0.5	9627
0.5-0.6	4949
0.6-0.7	9737
0.7-0.8	3299
0.8-0.85	49
0.85-0.9	12
0.9-0.95	4
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9388	High Similarity	NPC476363
0.9133	High Similarity	NPC476340
0.9054	High Similarity	NPC476335
0.898	High Similarity	NPC472567
0.8926	High Similarity	NPC28724
0.8859	High Similarity	NPC163002
0.8726	High Similarity	NPC476277
0.8716	High Similarity	NPC476338
0.8716	High Similarity	NPC476359
0.8699	High Similarity	NPC474966
0.8645	High Similarity	NPC476337
0.8552	High Similarity	NPC470962
0.8531	High Similarity	NPC145769
0.8523	High Similarity	NPC474446
0.8462	Intermediate Similarity	NPC472565
0.8446	Intermediate Similarity	NPC28326
0.8431	Intermediate Similarity	NPC474414
0.8418	Intermediate Similarity	NPC476244
0.8392	Intermediate Similarity	NPC153453
0.8378	Intermediate Similarity	NPC46180
0.8333	Intermediate Similarity	NPC232883
0.8323	Intermediate Similarity	NPC476364
0.8322	Intermediate Similarity	NPC472564
0.8301	Intermediate Similarity	NPC475170
0.8252	Intermediate Similarity	NPC280399
0.8252	Intermediate Similarity	NPC233961
0.8252	Intermediate Similarity	NPC339621
0.8224	Intermediate Similarity	NPC30720
0.8219	Intermediate Similarity	NPC211386
0.8188	Intermediate Similarity	NPC51681
0.8182	Intermediate Similarity	NPC177830
0.8176	Intermediate Similarity	NPC44573
0.8176	Intermediate Similarity	NPC46947
0.817	Intermediate Similarity	NPC77598
0.817	Intermediate Similarity	NPC294972
0.817	Intermediate Similarity	NPC117463
0.8141	Intermediate Similarity	NPC327225
0.8138	Intermediate Similarity	NPC239302
0.8129	Intermediate Similarity	NPC62354
0.8121	Intermediate Similarity	NPC322021
0.8117	Intermediate Similarity	NPC474903
0.8105	Intermediate Similarity	NPC25496
0.8095	Intermediate Similarity	NPC72796
0.8095	Intermediate Similarity	NPC44245
0.8092	Intermediate Similarity	NPC207732
0.8079	Intermediate Similarity	NPC185607
0.8077	Intermediate Similarity	NPC151425
0.8056	Intermediate Similarity	NPC150809
0.8052	Intermediate Similarity	NPC299923
0.8052	Intermediate Similarity	NPC470511
0.8041	Intermediate Similarity	NPC471182
0.8039	Intermediate Similarity	NPC472560
0.8039	Intermediate Similarity	NPC213482
0.8039	Intermediate Similarity	NPC157133
0.8027	Intermediate Similarity	NPC37065
0.8026	Intermediate Similarity	NPC15743
0.8026	Intermediate Similarity	NPC16353
0.8026	Intermediate Similarity	NPC50696
0.8026	Intermediate Similarity	NPC476054
0.8014	Intermediate Similarity	NPC119985
0.8014	Intermediate Similarity	NPC474691
0.8014	Intermediate Similarity	NPC280476
0.8013	Intermediate Similarity	NPC58229
0.8013	Intermediate Similarity	NPC472279
0.8	Intermediate Similarity	NPC477410
0.8	Intermediate Similarity	NPC245891
0.8	Intermediate Similarity	NPC299010
0.8	Intermediate Similarity	NPC250076
0.8	Intermediate Similarity	NPC475095
0.8	Intermediate Similarity	NPC172673
0.8	Intermediate Similarity	NPC104876
0.8	Intermediate Similarity	NPC476058
0.7987	Intermediate Similarity	NPC310259
0.7987	Intermediate Similarity	NPC195919
0.7987	Intermediate Similarity	NPC120924
0.7987	Intermediate Similarity	NPC216314
0.7986	Intermediate Similarity	NPC304747
0.7975	Intermediate Similarity	NPC25127
0.7974	Intermediate Similarity	NPC105213
0.7974	Intermediate Similarity	NPC474158
0.7973	Intermediate Similarity	NPC95485
0.7973	Intermediate Similarity	NPC88065
0.7973	Intermediate Similarity	NPC208760
0.7973	Intermediate Similarity	NPC89504
0.7962	Intermediate Similarity	NPC220577
0.7961	Intermediate Similarity	NPC312256
0.7959	Intermediate Similarity	NPC327410
0.7959	Intermediate Similarity	NPC288743
0.7949	Intermediate Similarity	NPC69752
0.7947	Intermediate Similarity	NPC476334
0.7937	Intermediate Similarity	NPC310206
0.7935	Intermediate Similarity	NPC474999
0.7925	Intermediate Similarity	NPC234485
0.7922	Intermediate Similarity	NPC296575
0.7922	Intermediate Similarity	NPC224687
0.7922	Intermediate Similarity	NPC212697
0.7922	Intermediate Similarity	NPC471590
0.7922	Intermediate Similarity	NPC136278
0.7922	Intermediate Similarity	NPC30890
0.7917	Intermediate Similarity	NPC64948
0.7914	Intermediate Similarity	NPC187491
0.7914	Intermediate Similarity	NPC319200
0.7911	Intermediate Similarity	NPC288534
0.7908	Intermediate Similarity	NPC119663
0.7908	Intermediate Similarity	NPC475000
0.7908	Intermediate Similarity	NPC18211
0.7898	Intermediate Similarity	NPC178048
0.7898	Intermediate Similarity	NPC201547
0.7898	Intermediate Similarity	NPC5840
0.7898	Intermediate Similarity	NPC259058
0.7898	Intermediate Similarity	NPC189270
0.7895	Intermediate Similarity	NPC110419
0.7895	Intermediate Similarity	NPC176586
0.7895	Intermediate Similarity	NPC210354
0.7885	Intermediate Similarity	NPC10304
0.7885	Intermediate Similarity	NPC63256
0.7872	Intermediate Similarity	NPC477886
0.7871	Intermediate Similarity	NPC165389
0.7871	Intermediate Similarity	NPC476336
0.7867	Intermediate Similarity	NPC166184
0.7862	Intermediate Similarity	NPC127172
0.7862	Intermediate Similarity	NPC287504
0.7862	Intermediate Similarity	NPC473664
0.7862	Intermediate Similarity	NPC472408
0.7857	Intermediate Similarity	NPC476841
0.7857	Intermediate Similarity	NPC113089
0.7857	Intermediate Similarity	NPC474982
0.7857	Intermediate Similarity	NPC293201
0.7857	Intermediate Similarity	NPC182842
0.7857	Intermediate Similarity	NPC476843
0.7853	Intermediate Similarity	NPC302741
0.7852	Intermediate Similarity	NPC143649
0.7848	Intermediate Similarity	NPC78505
0.7848	Intermediate Similarity	NPC95498
0.7848	Intermediate Similarity	NPC272566
0.7848	Intermediate Similarity	NPC246566
0.7843	Intermediate Similarity	NPC106920
0.7843	Intermediate Similarity	NPC103752
0.7843	Intermediate Similarity	NPC273657
0.7843	Intermediate Similarity	NPC474288
0.784	Intermediate Similarity	NPC298093
0.7834	Intermediate Similarity	NPC238366
0.7834	Intermediate Similarity	NPC181250
0.7829	Intermediate Similarity	NPC19158
0.7826	Intermediate Similarity	NPC474990
0.7826	Intermediate Similarity	NPC268317
0.7821	Intermediate Similarity	NPC93034
0.7821	Intermediate Similarity	NPC52106
0.7821	Intermediate Similarity	NPC119660
0.7821	Intermediate Similarity	NPC262804
0.7821	Intermediate Similarity	NPC98009
0.7821	Intermediate Similarity	NPC40654
0.7821	Intermediate Similarity	NPC205522
0.7812	Intermediate Similarity	NPC188962
0.7812	Intermediate Similarity	NPC31018
0.7812	Intermediate Similarity	NPC42871
0.7812	Intermediate Similarity	NPC202249
0.7812	Intermediate Similarity	NPC284353
0.7812	Intermediate Similarity	NPC255807
0.7808	Intermediate Similarity	NPC153547
0.7806	Intermediate Similarity	NPC193779
0.7806	Intermediate Similarity	NPC474799
0.7805	Intermediate Similarity	NPC476822
0.7801	Intermediate Similarity	NPC225245
0.78	Intermediate Similarity	NPC209229
0.7799	Intermediate Similarity	NPC166201
0.7799	Intermediate Similarity	NPC304954
0.7799	Intermediate Similarity	NPC40033
0.7792	Intermediate Similarity	NPC239608
0.7792	Intermediate Similarity	NPC46161
0.7792	Intermediate Similarity	NPC143092
0.7792	Intermediate Similarity	NPC177644
0.7792	Intermediate Similarity	NPC191158
0.7792	Intermediate Similarity	NPC9966
0.7792	Intermediate Similarity	NPC70853
0.7791	Intermediate Similarity	NPC216092
0.7791	Intermediate Similarity	NPC165549
0.7786	Intermediate Similarity	NPC254625
0.7786	Intermediate Similarity	NPC475961
0.7785	Intermediate Similarity	NPC216917
0.7785	Intermediate Similarity	NPC155098
0.7778	Intermediate Similarity	NPC253481
0.7778	Intermediate Similarity	NPC173608
0.7778	Intermediate Similarity	NPC40237
0.7778	Intermediate Similarity	NPC31751
0.7778	Intermediate Similarity	NPC151423
0.7778	Intermediate Similarity	NPC195832
0.7778	Intermediate Similarity	NPC253722
0.7778	Intermediate Similarity	NPC55738
0.7771	Intermediate Similarity	NPC476342
0.7771	Intermediate Similarity	NPC42230
0.7771	Intermediate Similarity	NPC474948
0.7771	Intermediate Similarity	NPC261548
0.7764	Intermediate Similarity	NPC265511
0.7764	Intermediate Similarity	NPC470762
0.7764	Intermediate Similarity	NPC474167
0.7764	Intermediate Similarity	NPC472455
0.7764	Intermediate Similarity	NPC303255
0.7763	Intermediate Similarity	NPC4796
0.7763	Intermediate Similarity	NPC278076

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 NPC476362 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	397
0.1-0.2	925
0.2-0.3	1774
0.3-0.4	2787
0.4-0.5	1929
0.5-0.6	960
0.6-0.7	325
0.7-0.8	53
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
0.7935	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7875	Intermediate Similarity	NPD3882	Suspended
0.784	Intermediate Similarity	NPD5494	Approved
0.7805	Intermediate Similarity	NPD3926	Phase 2
0.7697	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7683	Intermediate Similarity	NPD1247	Approved
0.7673	Intermediate Similarity	NPD7028	Phase 2
0.7669	Intermediate Similarity	NPD919	Approved
0.7643	Intermediate Similarity	NPD5536	Phase 2
0.7593	Intermediate Similarity	NPD3817	Phase 2
0.747	Intermediate Similarity	NPD7199	Phase 2
0.7466	Intermediate Similarity	NPD1876	Approved
0.7423	Intermediate Similarity	NPD2801	Approved
0.7414	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7405	Intermediate Similarity	NPD6799	Approved
0.7396	Intermediate Similarity	NPD7473	Discontinued
0.7362	Intermediate Similarity	NPD1934	Approved
0.7362	Intermediate Similarity	NPD37	Approved
0.7357	Intermediate Similarity	NPD5283	Phase 1
0.7346	Intermediate Similarity	NPD6599	Discontinued
0.7321	Intermediate Similarity	NPD6232	Discontinued
0.7317	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.7317	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.729	Intermediate Similarity	NPD2796	Approved
0.7279	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7278	Intermediate Similarity	NPD5242	Approved
0.7273	Intermediate Similarity	NPD5353	Approved
0.7273	Intermediate Similarity	NPD5978	Approved
0.7273	Intermediate Similarity	NPD5977	Approved
0.725	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD2403	Approved
0.7235	Intermediate Similarity	NPD6166	Phase 2
0.7229	Intermediate Similarity	NPD4965	Approved
0.7229	Intermediate Similarity	NPD4966	Approved
0.7229	Intermediate Similarity	NPD4967	Phase 2
0.7219	Intermediate Similarity	NPD3027	Phase 3
0.7215	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7211	Intermediate Similarity	NPD2981	Phase 2
0.7211	Intermediate Similarity	NPD3972	Approved
0.7205	Intermediate Similarity	NPD1512	Approved
0.719	Intermediate Similarity	NPD1240	Approved
0.7188	Intermediate Similarity	NPD4357	Discontinued
0.7186	Intermediate Similarity	NPD7075	Discontinued
0.7184	Intermediate Similarity	NPD7685	Pre-registration
0.717	Intermediate Similarity	NPD6190	Approved
0.7162	Intermediate Similarity	NPD2983	Phase 2
0.7162	Intermediate Similarity	NPD2982	Phase 2
0.7152	Intermediate Similarity	NPD6801	Discontinued
0.7151	Intermediate Similarity	NPD3818	Discontinued
0.7143	Intermediate Similarity	NPD6234	Discontinued
0.7143	Intermediate Similarity	NPD230	Phase 1
0.7126	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD3748	Approved
0.7115	Intermediate Similarity	NPD1510	Phase 2
0.711	Intermediate Similarity	NPD5844	Phase 1
0.7108	Intermediate Similarity	NPD7819	Suspended
0.7097	Intermediate Similarity	NPD1607	Approved
0.7091	Intermediate Similarity	NPD5090	Approved
0.7091	Intermediate Similarity	NPD5089	Approved
0.7089	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD9494	Approved
0.7086	Intermediate Similarity	NPD3018	Phase 2
0.7081	Intermediate Similarity	NPD1511	Approved
0.707	Intermediate Similarity	NPD6099	Approved
0.707	Intermediate Similarity	NPD6100	Approved
0.7059	Intermediate Similarity	NPD8127	Discontinued
0.7059	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD1651	Approved
0.7044	Intermediate Similarity	NPD2800	Approved
0.7037	Intermediate Similarity	NPD3146	Approved
0.7037	Intermediate Similarity	NPD3688	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6355	Discontinued
0.703	Intermediate Similarity	NPD4380	Phase 2
0.7025	Intermediate Similarity	NPD5763	Approved
0.7025	Intermediate Similarity	NPD5762	Approved
0.7007	Intermediate Similarity	NPD17	Approved
0.7006	Intermediate Similarity	NPD4585	Approved
0.7	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4110	Phase 3
0.6993	Remote Similarity	NPD1241	Discontinued
0.6988	Remote Similarity	NPD6385	Approved
0.6988	Remote Similarity	NPD6386	Approved
0.6987	Remote Similarity	NPD6651	Approved
0.6968	Remote Similarity	NPD943	Approved
0.6954	Remote Similarity	NPD3751	Discontinued
0.6951	Remote Similarity	NPD920	Approved
0.6949	Remote Similarity	NPD4338	Clinical (unspecified phase)
0.6949	Remote Similarity	NPD7808	Phase 3
0.6937	Remote Similarity	NPD1243	Approved
0.6933	Remote Similarity	NPD2532	Approved
0.6933	Remote Similarity	NPD2534	Approved
0.6933	Remote Similarity	NPD2533	Approved
0.6933	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6932	Remote Similarity	NPD6797	Phase 2
0.6932	Remote Similarity	NPD7993	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD3657	Discovery
0.6918	Remote Similarity	NPD1471	Phase 3
0.6913	Remote Similarity	NPD3705	Approved
0.6905	Remote Similarity	NPD1465	Phase 2
0.6903	Remote Similarity	NPD8032	Phase 2
0.6899	Remote Similarity	NPD651	Clinical (unspecified phase)
0.6894	Remote Similarity	NPD4628	Phase 3
0.6894	Remote Similarity	NPD3750	Approved
0.6893	Remote Similarity	NPD7251	Discontinued
0.6875	Remote Similarity	NPD7074	Phase 3
0.6875	Remote Similarity	NPD1549	Phase 2
0.6871	Remote Similarity	NPD5297	Approved
0.6867	Remote Similarity	NPD1608	Approved
0.6864	Remote Similarity	NPD5402	Approved
0.6864	Remote Similarity	NPD8443	Clinical (unspecified phase)
0.6859	Remote Similarity	NPD3620	Phase 2
0.6859	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6857	Remote Similarity	NPD7228	Approved
0.6852	Remote Similarity	NPD3887	Approved
0.6842	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6111	Discontinued
0.6832	Remote Similarity	NPD2654	Approved
0.6829	Remote Similarity	NPD642	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD3787	Discontinued
0.6818	Remote Similarity	NPD7054	Approved
0.6813	Remote Similarity	NPD2355	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD2353	Approved
0.681	Remote Similarity	NPD643	Clinical (unspecified phase)
0.681	Remote Similarity	NPD7124	Phase 2
0.68	Remote Similarity	NPD1281	Approved
0.6798	Remote Similarity	NPD6764	Approved
0.6798	Remote Similarity	NPD6765	Approved
0.6797	Remote Similarity	NPD4624	Approved
0.6788	Remote Similarity	NPD6273	Approved
0.6786	Remote Similarity	NPD6873	Phase 2
0.6786	Remote Similarity	NPD7411	Suspended
0.678	Remote Similarity	NPD7472	Approved
0.6774	Remote Similarity	NPD7095	Approved
0.675	Remote Similarity	NPD2438	Suspended
0.675	Remote Similarity	NPD2935	Discontinued
0.6748	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6747	Remote Similarity	NPD5403	Approved
0.6732	Remote Similarity	NPD3267	Approved
0.6732	Remote Similarity	NPD3266	Approved
0.6731	Remote Similarity	NPD1296	Phase 2
0.6728	Remote Similarity	NPD7421	Clinical (unspecified phase)
0.6727	Remote Similarity	NPD5401	Approved
0.6725	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6724	Remote Similarity	NPD7229	Phase 3
0.6723	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD3534	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD5327	Phase 3
0.6711	Remote Similarity	NPD3024	Approved
0.6711	Remote Similarity	NPD4749	Approved
0.6711	Remote Similarity	NPD3025	Approved
0.6711	Remote Similarity	NPD9268	Approved
0.671	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD447	Suspended
0.6708	Remote Similarity	NPD6002	Phase 3
0.6708	Remote Similarity	NPD6006	Clinical (unspecified phase)
0.6708	Remote Similarity	NPD6004	Phase 3
0.6708	Remote Similarity	NPD6005	Phase 3
0.6708	Remote Similarity	NPD6003	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD7236	Approved
0.6706	Remote Similarity	NPD5761	Phase 2
0.6706	Remote Similarity	NPD5760	Phase 2
0.6704	Remote Similarity	NPD7240	Approved
0.6703	Remote Similarity	NPD8434	Phase 2
0.6688	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6688	Remote Similarity	NPD5647	Approved
0.6687	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD2799	Discontinued
0.6687	Remote Similarity	NPD8166	Discontinued
0.6686	Remote Similarity	NPD3749	Approved
0.6686	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD1283	Approved
0.6667	Remote Similarity	NPD2424	Discontinued
0.6667	Remote Similarity	NPD2932	Approved
0.6667	Remote Similarity	NPD6653	Approved
0.6648	Remote Similarity	NPD6784	Approved
0.6648	Remote Similarity	NPD6785	Approved
0.6646	Remote Similarity	NPD3539	Phase 1
0.6646	Remote Similarity	NPD2354	Approved
0.6646	Remote Similarity	NPD2979	Phase 3
0.6646	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6646	Remote Similarity	NPD4060	Phase 1
0.6646	Remote Similarity	NPD1613	Approved
0.6645	Remote Similarity	NPD9269	Phase 2
0.6645	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.663	Remote Similarity	NPD2971	Approved
0.663	Remote Similarity	NPD2968	Approved
0.6627	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD3268	Approved
0.6624	Remote Similarity	NPD6798	Discontinued
0.6623	Remote Similarity	NPD3026	Approved
0.6623	Remote Similarity	NPD3023	Approved
0.6621	Remote Similarity	NPD228	Approved
0.6605	Remote Similarity	NPD2344	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