NPASS Compound

Structure

NPC306727 OpenBabel07101719242D 23 24 0 0 1 0 0 0 0 0999 V2000 0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3660 2.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -2.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 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 -0.0000 -5.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 14 2 0 0 0 0 3 19 1 0 0 0 0 4 19 1 0 0 0 0 6 8 1 0 0 0 0 6 9 1 0 0 0 0 7 10 1 0 0 0 0 7 13 2 0 0 0 0 8 19 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 15 1 0 0 0 0 11 16 1 0 0 0 0 12 17 1 0 0 0 0 12 18 1 0 0 0 0 13 16 1 0 0 0 0 14 15 1 0 0 0 0 14 17 1 0 0 0 0 15 20 1 1 0 0 0 16 22 1 1 0 0 0 17 23 1 6 0 0 0 18 19 1 0 0 0 0 18 20 1 1 0 0 0 20 5 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	322.25
Volume:	358.461
LogP:	2.305
LogD:	2.58
LogS:	-3.69
# Rotatable Bonds:	4
TPSA:	60.69
# H-Bond Aceptor:	3
# H-Bond Donor:	3
# Rings:	2
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.695
Synthetic Accessibility Score:	4.685
Fsp3:	0.8
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-4.691
MDCK Permeability:	2.0275187125662342e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.766
Human Intestinal Absorption (HIA):	0.038
20% Bioavailability (F20%):	0.864
30% Bioavailability (F30%):	0.626

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.074
Plasma Protein Binding (PPB):	68.4868392944336%
Volume Distribution (VD):	1.283
Pgp-substrate:	27.023591995239258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.021
CYP1A2-substrate:	0.114
CYP2C19-inhibitor:	0.019
CYP2C19-substrate:	0.707
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.368
CYP2D6-inhibitor:	0.004
CYP2D6-substrate:	0.236
CYP3A4-inhibitor:	0.049
CYP3A4-substrate:	0.22

ADMET: Excretion

Clearance (CL):	5.01
Half-life (T1/2):	0.16

ADMET: Toxicity

hERG Blockers:	0.048
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.029
AMES Toxicity:	0.008
Rat Oral Acute Toxicity:	0.693
Maximum Recommended Daily Dose:	0.993
Skin Sensitization:	0.721
Carcinogencity:	0.051
Eye Corrosion:	0.511
Eye Irritation:	0.94
Respiratory Toxicity:	0.947

Download Data

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

Natural Product: NPC306727

Natural Product ID:	NPC306727
*Common Name:**	Physordin
IUPAC Name:	(E,4R)-5-[(1R,3R,4aS,8aS)-3-hydroxy-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]-3-methylpent-2-ene-1,4-diol
Synonyms:	Physordin
Standard InCHIKey:	BRBJHQRWXQRMLL-PQGOTGDCSA-N
Standard InCHI:	InChI=1S/C20H34O3/c1-13(7-10-21)16(22)11-15-14(2)17(23)12-18-19(3,4)8-6-9-20(15,18)5/h7,15-18,21-23H,2,6,8-12H2,1,3-5H3/b13-7+/t15-,16+,17+,18-,20+/m0/s1
SMILES:	C/C(=CCO)/[C@@H](C[C@H]1C(=C)[C@@H](C[C@H]2C(C)(C)CCC[C@]12C)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1173546
PubChem CID:	46873722
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO23525	Physalis sordida	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20575572]
NPO23525	Physalis sordida	Species	Solanaceae	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
Others	1

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	Inhibition	=	64.3	%	PMID[495529]
NPT32	Organism	Mus musculus	Mus musculus	IC50	=	630.0	nM	PMID[495529]

☑ 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 NPC306727 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	174
0.1-0.2	1356
0.2-0.3	5259
0.3-0.4	14794
0.4-0.5	9874
0.5-0.6	6491
0.6-0.7	3552
0.7-0.8	989
0.8-0.85	143
0.85-0.9	45
0.9-0.95	18
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9437	High Similarity	NPC253190
0.9296	High Similarity	NPC32832
0.9189	High Similarity	NPC96362
0.9155	High Similarity	NPC476366
0.9155	High Similarity	NPC201048
0.9118	High Similarity	NPC69649
0.9118	High Similarity	NPC68703
0.9067	High Similarity	NPC249423
0.9067	High Similarity	NPC476646
0.9041	High Similarity	NPC470711
0.9041	High Similarity	NPC470758
0.9	High Similarity	NPC34834
0.8919	High Similarity	NPC476314
0.8904	High Similarity	NPC470749
0.8873	High Similarity	NPC167706
0.8857	High Similarity	NPC9942
0.8816	High Similarity	NPC209620
0.8816	High Similarity	NPC23852
0.88	High Similarity	NPC30986
0.88	High Similarity	NPC209430
0.8784	High Similarity	NPC91594
0.8784	High Similarity	NPC471798
0.875	High Similarity	NPC68443
0.8718	High Similarity	NPC102048
0.8714	High Similarity	NPC471238
0.8714	High Similarity	NPC245795
0.8714	High Similarity	NPC96484
0.8701	High Similarity	NPC50964
0.8684	High Similarity	NPC295131
0.8684	High Similarity	NPC281880
0.8667	High Similarity	NPC83351
0.8667	High Similarity	NPC167891
0.8667	High Similarity	NPC11908
0.8649	High Similarity	NPC265588
0.863	High Similarity	NPC243342
0.863	High Similarity	NPC91858
0.863	High Similarity	NPC469593
0.863	High Similarity	NPC477138
0.863	High Similarity	NPC469534
0.863	High Similarity	NPC469533
0.8611	High Similarity	NPC477792
0.8611	High Similarity	NPC242001
0.8571	High Similarity	NPC159148
0.8553	High Similarity	NPC472463
0.8553	High Similarity	NPC143182
0.8553	High Similarity	NPC28862
0.8553	High Similarity	NPC47982
0.8553	High Similarity	NPC84694
0.8553	High Similarity	NPC81306
0.8553	High Similarity	NPC109546
0.8533	High Similarity	NPC130136
0.8514	High Similarity	NPC291503
0.8514	High Similarity	NPC66566
0.8514	High Similarity	NPC477923
0.85	High Similarity	NPC6391
0.85	High Similarity	NPC261266
0.8493	Intermediate Similarity	NPC471799
0.8493	Intermediate Similarity	NPC182717
0.8472	Intermediate Similarity	NPC145498
0.8462	Intermediate Similarity	NPC155521
0.8462	Intermediate Similarity	NPC218616
0.8462	Intermediate Similarity	NPC296701
0.8451	Intermediate Similarity	NPC208999
0.8442	Intermediate Similarity	NPC287749
0.8442	Intermediate Similarity	NPC234193
0.8429	Intermediate Similarity	NPC476406
0.8421	Intermediate Similarity	NPC87604
0.8421	Intermediate Similarity	NPC474216
0.8406	Intermediate Similarity	NPC225415
0.8406	Intermediate Similarity	NPC68656
0.84	Intermediate Similarity	NPC244488
0.84	Intermediate Similarity	NPC274079
0.84	Intermediate Similarity	NPC247325
0.84	Intermediate Similarity	NPC477925
0.8395	Intermediate Similarity	NPC476948
0.8378	Intermediate Similarity	NPC100334
0.8378	Intermediate Similarity	NPC471797
0.8375	Intermediate Similarity	NPC470360
0.8356	Intermediate Similarity	NPC471272
0.8356	Intermediate Similarity	NPC471271
0.8356	Intermediate Similarity	NPC23954
0.8356	Intermediate Similarity	NPC471268
0.8354	Intermediate Similarity	NPC317458
0.8333	Intermediate Similarity	NPC471560
0.8333	Intermediate Similarity	NPC242350
0.8333	Intermediate Similarity	NPC264245
0.8333	Intermediate Similarity	NPC474248
0.831	Intermediate Similarity	NPC253303
0.831	Intermediate Similarity	NPC114651
0.831	Intermediate Similarity	NPC269077
0.8293	Intermediate Similarity	NPC133588
0.8293	Intermediate Similarity	NPC474668
0.8289	Intermediate Similarity	NPC34177
0.8289	Intermediate Similarity	NPC157996
0.8289	Intermediate Similarity	NPC472805
0.8289	Intermediate Similarity	NPC101475
0.8289	Intermediate Similarity	NPC40394
0.8289	Intermediate Similarity	NPC90979
0.8289	Intermediate Similarity	NPC477924
0.8272	Intermediate Similarity	NPC139724
0.8272	Intermediate Similarity	NPC152808
0.8272	Intermediate Similarity	NPC293287
0.8272	Intermediate Similarity	NPC299068
0.8272	Intermediate Similarity	NPC472985
0.8272	Intermediate Similarity	NPC472986
0.8267	Intermediate Similarity	NPC69383
0.8267	Intermediate Similarity	NPC141071
0.8267	Intermediate Similarity	NPC471723
0.8267	Intermediate Similarity	NPC313179
0.8267	Intermediate Similarity	NPC257347
0.8267	Intermediate Similarity	NPC171148
0.825	Intermediate Similarity	NPC474047
0.8243	Intermediate Similarity	NPC220939
0.8243	Intermediate Similarity	NPC474743
0.8243	Intermediate Similarity	NPC265485
0.8228	Intermediate Similarity	NPC304285
0.8228	Intermediate Similarity	NPC49964
0.8228	Intermediate Similarity	NPC101462
0.8228	Intermediate Similarity	NPC248886
0.8228	Intermediate Similarity	NPC2524
0.8228	Intermediate Similarity	NPC202389
0.8228	Intermediate Similarity	NPC87489
0.8228	Intermediate Similarity	NPC470049
0.8228	Intermediate Similarity	NPC189972
0.8219	Intermediate Similarity	NPC92801
0.8219	Intermediate Similarity	NPC189745
0.8219	Intermediate Similarity	NPC283316
0.8205	Intermediate Similarity	NPC164840
0.8205	Intermediate Similarity	NPC209944
0.8205	Intermediate Similarity	NPC324772
0.8205	Intermediate Similarity	NPC26117
0.8205	Intermediate Similarity	NPC241290
0.8194	Intermediate Similarity	NPC276616
0.8193	Intermediate Similarity	NPC470361
0.8193	Intermediate Similarity	NPC259875
0.8193	Intermediate Similarity	NPC187785
0.8193	Intermediate Similarity	NPC477917
0.8182	Intermediate Similarity	NPC230295
0.8182	Intermediate Similarity	NPC244385
0.8182	Intermediate Similarity	NPC472500
0.8182	Intermediate Similarity	NPC473943
0.8182	Intermediate Similarity	NPC98386
0.8182	Intermediate Similarity	NPC22955
0.8182	Intermediate Similarity	NPC196753
0.8182	Intermediate Similarity	NPC285761
0.8182	Intermediate Similarity	NPC158662
0.8182	Intermediate Similarity	NPC99168
0.8182	Intermediate Similarity	NPC472499
0.8182	Intermediate Similarity	NPC253807
0.8182	Intermediate Similarity	NPC474989
0.8182	Intermediate Similarity	NPC167037
0.8182	Intermediate Similarity	NPC138621
0.8182	Intermediate Similarity	NPC470396
0.8182	Intermediate Similarity	NPC6978
0.8182	Intermediate Similarity	NPC300499
0.8182	Intermediate Similarity	NPC148977
0.8169	Intermediate Similarity	NPC475897
0.8169	Intermediate Similarity	NPC202017
0.8169	Intermediate Similarity	NPC149680
0.8158	Intermediate Similarity	NPC107059
0.8158	Intermediate Similarity	NPC30590
0.8158	Intermediate Similarity	NPC321016
0.8158	Intermediate Similarity	NPC129165
0.8158	Intermediate Similarity	NPC27765
0.8158	Intermediate Similarity	NPC106432
0.8158	Intermediate Similarity	NPC237460
0.8158	Intermediate Similarity	NPC189883
0.8158	Intermediate Similarity	NPC321381
0.8158	Intermediate Similarity	NPC122418
0.8158	Intermediate Similarity	NPC265328
0.8158	Intermediate Similarity	NPC120098
0.8158	Intermediate Similarity	NPC63958
0.8158	Intermediate Similarity	NPC290598
0.8158	Intermediate Similarity	NPC134330
0.8143	Intermediate Similarity	NPC144650
0.8143	Intermediate Similarity	NPC290367
0.8133	Intermediate Similarity	NPC472503
0.8133	Intermediate Similarity	NPC308440
0.8125	Intermediate Similarity	NPC79945
0.8125	Intermediate Similarity	NPC474634
0.8125	Intermediate Similarity	NPC82623
0.8125	Intermediate Similarity	NPC113978
0.8125	Intermediate Similarity	NPC477818
0.8125	Intermediate Similarity	NPC475789
0.8125	Intermediate Similarity	NPC110778
0.8108	Intermediate Similarity	NPC164022
0.8108	Intermediate Similarity	NPC110799
0.8101	Intermediate Similarity	NPC474752
0.8101	Intermediate Similarity	NPC474759
0.8101	Intermediate Similarity	NPC474731
0.8101	Intermediate Similarity	NPC474683
0.8101	Intermediate Similarity	NPC82986
0.8101	Intermediate Similarity	NPC47761
0.8101	Intermediate Similarity	NPC7505
0.8101	Intermediate Similarity	NPC170303
0.8101	Intermediate Similarity	NPC470383
0.8101	Intermediate Similarity	NPC320525
0.8095	Intermediate Similarity	NPC295668
0.8095	Intermediate Similarity	NPC80561
0.8095	Intermediate Similarity	NPC11216

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 NPC306727 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	156
0.1-0.2	1720
0.2-0.3	4008
0.3-0.4	2237
0.4-0.5	632
0.5-0.6	262
0.6-0.7	90
0.7-0.8	41
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8312	Intermediate Similarity	NPD6929	Approved
0.8267	Intermediate Similarity	NPD8264	Approved
0.8205	Intermediate Similarity	NPD6930	Phase 2
0.8205	Intermediate Similarity	NPD6931	Approved
0.8077	Intermediate Similarity	NPD7645	Phase 2
0.8052	Intermediate Similarity	NPD5776	Phase 2
0.8052	Intermediate Similarity	NPD6925	Approved
0.8026	Intermediate Similarity	NPD7339	Approved
0.8026	Intermediate Similarity	NPD6942	Approved
0.7975	Intermediate Similarity	NPD7514	Phase 3
0.7975	Intermediate Similarity	NPD7332	Phase 2
0.7975	Intermediate Similarity	NPD7525	Registered
0.7952	Intermediate Similarity	NPD4751	Clinical (unspecified phase)
0.7949	Intermediate Similarity	NPD7145	Approved
0.7922	Intermediate Similarity	NPD3701	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6695	Phase 3
0.7895	Intermediate Similarity	NPD6926	Approved
0.7895	Intermediate Similarity	NPD6924	Approved
0.7875	Intermediate Similarity	NPD6902	Approved
0.7805	Intermediate Similarity	NPD7338	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD7322	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD6893	Approved
0.7692	Intermediate Similarity	NPD6933	Approved
0.7654	Intermediate Similarity	NPD6898	Phase 1
0.7632	Intermediate Similarity	NPD7150	Approved
0.7632	Intermediate Similarity	NPD7152	Approved
0.7632	Intermediate Similarity	NPD7151	Approved
0.76	Intermediate Similarity	NPD6922	Approved
0.76	Intermediate Similarity	NPD6923	Approved
0.7595	Intermediate Similarity	NPD6932	Approved
0.7531	Intermediate Similarity	NPD7509	Discontinued
0.7529	Intermediate Similarity	NPD7524	Approved
0.7529	Intermediate Similarity	NPD7750	Discontinued
0.75	Intermediate Similarity	NPD7144	Approved
0.75	Intermediate Similarity	NPD7143	Approved
0.7407	Intermediate Similarity	NPD6683	Phase 2
0.7391	Intermediate Similarity	NPD7640	Approved
0.7391	Intermediate Similarity	NPD7639	Approved
0.7381	Intermediate Similarity	NPD4786	Approved
0.7349	Intermediate Similarity	NPD3667	Approved
0.7283	Intermediate Similarity	NPD7638	Approved
0.7209	Intermediate Similarity	NPD3618	Phase 1
0.7191	Intermediate Similarity	NPD7087	Discontinued
0.7179	Intermediate Similarity	NPD4243	Approved
0.7159	Intermediate Similarity	NPD5328	Approved
0.7123	Intermediate Similarity	NPD368	Approved
0.7	Intermediate Similarity	NPD342	Phase 1
0.7	Intermediate Similarity	NPD4784	Approved
0.7	Intermediate Similarity	NPD6079	Approved
0.7	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD7515	Phase 2
0.7	Intermediate Similarity	NPD4785	Approved
0.6977	Remote Similarity	NPD3133	Approved
0.6977	Remote Similarity	NPD3665	Phase 1
0.6977	Remote Similarity	NPD3666	Approved
0.6915	Remote Similarity	NPD4225	Approved
0.6905	Remote Similarity	NPD4748	Discontinued
0.6889	Remote Similarity	NPD7136	Phase 2
0.6875	Remote Similarity	NPD4732	Discontinued
0.6739	Remote Similarity	NPD4202	Approved
0.6739	Remote Similarity	NPD5778	Approved
0.6739	Remote Similarity	NPD5779	Approved
0.6707	Remote Similarity	NPD4190	Phase 3
0.6707	Remote Similarity	NPD5275	Approved
0.6705	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD7632	Discontinued
0.6667	Remote Similarity	NPD4219	Approved
0.6667	Remote Similarity	NPD7748	Approved
0.6629	Remote Similarity	NPD4519	Discontinued
0.6629	Remote Similarity	NPD5279	Phase 3
0.6629	Remote Similarity	NPD4623	Approved
0.6591	Remote Similarity	NPD3668	Phase 3
0.6588	Remote Similarity	NPD4195	Approved
0.6559	Remote Similarity	NPD6399	Phase 3
0.6531	Remote Similarity	NPD5211	Phase 2
0.6526	Remote Similarity	NPD5221	Approved
0.6526	Remote Similarity	NPD4697	Phase 3
0.6526	Remote Similarity	NPD5222	Approved
0.6526	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6512	Remote Similarity	NPD4695	Discontinued
0.6471	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD5173	Approved
0.6458	Remote Similarity	NPD4755	Approved
0.6458	Remote Similarity	NPD7902	Approved
0.6429	Remote Similarity	NPD5344	Discontinued
0.6413	Remote Similarity	NPD4753	Phase 2
0.6413	Remote Similarity	NPD6051	Approved
0.64	Remote Similarity	NPD5141	Approved
0.6392	Remote Similarity	NPD5290	Discontinued
0.6373	Remote Similarity	NPD6686	Approved
0.6364	Remote Similarity	NPD4223	Phase 3
0.6364	Remote Similarity	NPD4221	Approved
0.6364	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD6640	Phase 3
0.6333	Remote Similarity	NPD5329	Approved
0.6333	Remote Similarity	NPD1696	Phase 3
0.6327	Remote Similarity	NPD4696	Approved
0.6327	Remote Similarity	NPD5285	Approved
0.6327	Remote Similarity	NPD5286	Approved
0.6327	Remote Similarity	NPD4700	Approved
0.6322	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD4788	Approved
0.6277	Remote Similarity	NPD6411	Approved
0.6264	Remote Similarity	NPD7146	Approved
0.6264	Remote Similarity	NPD5330	Approved
0.6264	Remote Similarity	NPD7521	Approved
0.6264	Remote Similarity	NPD6684	Approved
0.6264	Remote Similarity	NPD7334	Approved
0.6264	Remote Similarity	NPD6409	Approved
0.6263	Remote Similarity	NPD5223	Approved
0.6222	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6222	Remote Similarity	NPD4197	Approved
0.622	Remote Similarity	NPD4787	Phase 1
0.62	Remote Similarity	NPD5225	Approved
0.62	Remote Similarity	NPD5226	Approved
0.62	Remote Similarity	NPD5224	Approved
0.62	Remote Similarity	NPD4633	Approved
0.6176	Remote Similarity	NPD6402	Approved
0.6176	Remote Similarity	NPD5739	Approved
0.6176	Remote Similarity	NPD7128	Approved
0.6176	Remote Similarity	NPD4265	Approved
0.6176	Remote Similarity	NPD6675	Approved
0.6162	Remote Similarity	NPD6648	Approved
0.6147	Remote Similarity	NPD7327	Approved
0.6147	Remote Similarity	NPD7328	Approved
0.6146	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6146	Remote Similarity	NPD7900	Approved
0.6145	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6139	Remote Similarity	NPD5174	Approved
0.6139	Remote Similarity	NPD5175	Approved
0.6139	Remote Similarity	NPD4754	Approved
0.6136	Remote Similarity	NPD4822	Approved
0.6136	Remote Similarity	NPD4820	Approved
0.6136	Remote Similarity	NPD4819	Approved
0.6136	Remote Similarity	NPD4821	Approved
0.6129	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6129	Remote Similarity	NPD6903	Approved
0.6122	Remote Similarity	NPD6084	Phase 2
0.6122	Remote Similarity	NPD6083	Phase 2
0.6118	Remote Similarity	NPD3703	Phase 2
0.6117	Remote Similarity	NPD6412	Phase 2
0.6111	Remote Similarity	NPD5362	Discontinued
0.6111	Remote Similarity	NPD5332	Approved
0.6111	Remote Similarity	NPD5331	Approved
0.6105	Remote Similarity	NPD8034	Phase 2
0.6105	Remote Similarity	NPD8035	Phase 2
0.61	Remote Similarity	NPD4159	Approved
0.6098	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.6098	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.6095	Remote Similarity	NPD4634	Approved
0.6092	Remote Similarity	NPD6115	Approved
0.6092	Remote Similarity	NPD3617	Approved
0.6092	Remote Similarity	NPD6118	Approved
0.6092	Remote Similarity	NPD4268	Approved
0.6092	Remote Similarity	NPD6114	Approved
0.6092	Remote Similarity	NPD4271	Approved
0.6092	Remote Similarity	NPD6697	Approved
0.6091	Remote Similarity	NPD7516	Approved
0.6087	Remote Similarity	NPD4690	Approved
0.6087	Remote Similarity	NPD4138	Approved
0.6087	Remote Similarity	NPD4693	Phase 3
0.6087	Remote Similarity	NPD4688	Approved
0.6087	Remote Similarity	NPD4689	Approved
0.6087	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5205	Approved
0.6082	Remote Similarity	NPD5210	Approved
0.6082	Remote Similarity	NPD4629	Approved
0.6067	Remote Similarity	NPD4790	Discontinued
0.6064	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6064	Remote Similarity	NPD6101	Approved
0.6058	Remote Similarity	NPD6881	Approved
0.6058	Remote Similarity	NPD6899	Approved
0.6058	Remote Similarity	NPD7320	Approved
0.6055	Remote Similarity	NPD7115	Discovery
0.6036	Remote Similarity	NPD8377	Approved
0.6036	Remote Similarity	NPD8294	Approved
0.6019	Remote Similarity	NPD7333	Discontinued
0.6019	Remote Similarity	NPD4768	Approved
0.6019	Remote Similarity	NPD4767	Approved
0.6	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6	Remote Similarity	NPD6372	Approved
0.6	Remote Similarity	NPD4269	Approved
0.6	Remote Similarity	NPD4270	Approved
0.6	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.6	Remote Similarity	NPD3168	Discontinued
0.6	Remote Similarity	NPD6373	Approved
0.5982	Remote Similarity	NPD8380	Approved
0.5982	Remote Similarity	NPD8033	Approved
0.5982	Remote Similarity	NPD8296	Approved
0.5982	Remote Similarity	NPD8378	Approved
0.5982	Remote Similarity	NPD8379	Approved
0.5982	Remote Similarity	NPD8335	Approved
0.5962	Remote Similarity	NPD5697	Approved
0.5962	Remote Similarity	NPD5701	Approved
0.5957	Remote Similarity	NPD6672	Approved
0.5957	Remote Similarity	NPD5737	Approved
0.5957	Remote Similarity	NPD4723	Approved
0.5957	Remote Similarity	NPD4722	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