NPASS Compound

Structure

NPC31936 OpenBabel07101718292D 24 26 0 0 1 0 0 0 0 0999 V2000 3.5668 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0215 -1.7045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4311 0.9757 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5668 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3237 -2.1477 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8198 0.8836 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4749 0.3730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8347 -0.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6328 -1.6123 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0462 -0.6164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7008 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1796 -1.1919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0218 0.7935 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8347 -1.7024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2235 -1.7945 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7008 -2.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8586 -2.1878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3091 0.5353 0.0000 C 0 0 0 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 2.5218 1.6595 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7008 -3.2024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2240 -3.1186 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4240 1.2155 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9556 0.2948 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 2 0 0 0 0 1 11 1 0 0 0 0 2 5 2 0 0 0 0 2 12 1 0 0 0 0 3 6 1 0 0 0 0 3 13 1 0 0 0 0 4 16 1 0 0 0 0 5 17 1 0 0 0 0 6 18 1 0 0 0 0 7 11 1 0 0 0 0 7 13 1 0 0 0 0 8 11 2 0 0 0 0 8 14 1 0 0 0 0 9 12 2 0 0 0 0 9 15 1 0 0 0 0 10 12 1 0 0 0 0 10 19 1 0 0 0 0 13 20 1 6 0 0 0 14 15 1 0 0 0 0 14 16 2 0 0 0 0 15 17 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 19 1 0 0 0 0 18 23 2 0 0 0 0 19 24 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	328.13
Volume:	337.007
LogP:	1.892
LogD:	1.489
LogS:	-3.061
# Rotatable Bonds:	0
TPSA:	97.99
# H-Bond Aceptor:	5
# H-Bond Donor:	4
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.592
Synthetic Accessibility Score:	5.044
Fsp3:	0.316
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:	-4.76
MDCK Permeability:	9.923284778778907e-06
Pgp-inhibitor:	0.005
Pgp-substrate:	0.994
Human Intestinal Absorption (HIA):	0.019
20% Bioavailability (F20%):	0.998
30% Bioavailability (F30%):	0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.056
Plasma Protein Binding (PPB):	90.8275375366211%
Volume Distribution (VD):	0.645
Pgp-substrate:	21.54648780822754%

ADMET: Metabolism

CYP1A2-inhibitor:	0.499
CYP1A2-substrate:	0.364
CYP2C19-inhibitor:	0.153
CYP2C19-substrate:	0.067
CYP2C9-inhibitor:	0.22
CYP2C9-substrate:	0.837
CYP2D6-inhibitor:	0.321
CYP2D6-substrate:	0.755
CYP3A4-inhibitor:	0.192
CYP3A4-substrate:	0.27

ADMET: Excretion

Clearance (CL):	15.907
Half-life (T1/2):	0.867

ADMET: Toxicity

hERG Blockers:	0.081
Human Hepatotoxicity (H-HT):	0.265
Drug-inuced Liver Injury (DILI):	0.063
AMES Toxicity:	0.222
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.475
Carcinogencity:	0.134
Eye Corrosion:	0.003
Eye Irritation:	0.089
Respiratory Toxicity:	0.063

Download Data

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

Natural Product: NPC31936

Natural Product ID:	NPC31936
*Common Name:**	Casuarinondiol
IUPAC Name:	n.a.
Synonyms:	Casuarinondiol
Standard InCHIKey:	QYTZDHMMNGJCNX-ORAYPTAESA-N
Standard InCHI:	InChI=1S/C19H20O5/c20-13-3-6-18(23)19(24)10-12-2-5-17(22)15(9-12)14-8-11(7-13)1-4-16(14)21/h1-2,4-5,8-9,13,19-22,24H,3,6-7,10H2/t13-,19+/m0/s1
SMILES:	c1cc(c2-c3cc(ccc3O)C[C@H](C(=O)CC[C@@H](Cc1c2)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL450805
PubChem CID:	14704507
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002650] Diarylheptanoids [CHEMONTID:0002652] Cyclic diarylheptanoids [CHEMONTID:0003524] Meta,meta-bridged biphenyls

*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
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	stems	n.a.	n.a.	PMID[12350169]
NPO12848	Carpinus cordata	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	>	100.0	ug.mL-1	PMID[466132]

☑ 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 NPC31936 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	281
0.1-0.2	1236
0.2-0.3	3030
0.3-0.4	8437
0.4-0.5	11265
0.5-0.6	5348
0.6-0.7	10219
0.7-0.8	2760
0.8-0.85	98
0.85-0.9	13
0.9-0.95	5
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9661	High Similarity	NPC127975
0.9652	High Similarity	NPC473136
0.9412	High Similarity	NPC231767
0.9397	High Similarity	NPC182240
0.9123	High Similarity	NPC286222
0.8803	High Similarity	NPC473137
0.8803	High Similarity	NPC12656
0.878	High Similarity	NPC474803
0.8772	High Similarity	NPC262365
0.8707	High Similarity	NPC308689
0.8707	High Similarity	NPC177576
0.8621	High Similarity	NPC252544
0.8621	High Similarity	NPC44732
0.8621	High Similarity	NPC321252
0.856	High Similarity	NPC87985
0.8487	Intermediate Similarity	NPC285350
0.8473	Intermediate Similarity	NPC61153
0.8473	Intermediate Similarity	NPC283590
0.8473	Intermediate Similarity	NPC70859
0.8473	Intermediate Similarity	NPC130899
0.8435	Intermediate Similarity	NPC188677
0.8421	Intermediate Similarity	NPC288411
0.8421	Intermediate Similarity	NPC8931
0.8421	Intermediate Similarity	NPC261573
0.8421	Intermediate Similarity	NPC120693
0.8387	Intermediate Similarity	NPC295034
0.8362	Intermediate Similarity	NPC228737
0.8348	Intermediate Similarity	NPC138942
0.8333	Intermediate Similarity	NPC181334
0.8333	Intermediate Similarity	NPC168829
0.8321	Intermediate Similarity	NPC213485
0.8321	Intermediate Similarity	NPC139074
0.8321	Intermediate Similarity	NPC40524
0.8321	Intermediate Similarity	NPC314048
0.8319	Intermediate Similarity	NPC228988
0.8306	Intermediate Similarity	NPC164852
0.8306	Intermediate Similarity	NPC216216
0.8293	Intermediate Similarity	NPC473767
0.8291	Intermediate Similarity	NPC317305
0.8276	Intermediate Similarity	NPC70843
0.8264	Intermediate Similarity	NPC23402
0.8254	Intermediate Similarity	NPC471187
0.8226	Intermediate Similarity	NPC34634
0.8226	Intermediate Similarity	NPC265454
0.822	Intermediate Similarity	NPC88141
0.8217	Intermediate Similarity	NPC476024
0.8182	Intermediate Similarity	NPC471749
0.8175	Intermediate Similarity	NPC475192
0.8175	Intermediate Similarity	NPC176208
0.8168	Intermediate Similarity	NPC475042
0.8154	Intermediate Similarity	NPC102829
0.8154	Intermediate Similarity	NPC120488
0.8151	Intermediate Similarity	NPC21162
0.8151	Intermediate Similarity	NPC475018
0.8145	Intermediate Similarity	NPC476020
0.8136	Intermediate Similarity	NPC95344
0.8129	Intermediate Similarity	NPC474799
0.812	Intermediate Similarity	NPC29989
0.812	Intermediate Similarity	NPC69332
0.812	Intermediate Similarity	NPC95178
0.811	Intermediate Similarity	NPC198014
0.8092	Intermediate Similarity	NPC123
0.8092	Intermediate Similarity	NPC163169
0.8087	Intermediate Similarity	NPC7686
0.8087	Intermediate Similarity	NPC40258
0.8087	Intermediate Similarity	NPC91461
0.808	Intermediate Similarity	NPC223451
0.8077	Intermediate Similarity	NPC24869
0.807	Intermediate Similarity	NPC132078
0.807	Intermediate Similarity	NPC78119
0.807	Intermediate Similarity	NPC216468
0.807	Intermediate Similarity	NPC51333
0.8067	Intermediate Similarity	NPC326187
0.8065	Intermediate Similarity	NPC104514
0.8065	Intermediate Similarity	NPC249435
0.8062	Intermediate Similarity	NPC474944
0.806	Intermediate Similarity	NPC152209
0.8049	Intermediate Similarity	NPC325646
0.8049	Intermediate Similarity	NPC28951
0.8043	Intermediate Similarity	NPC85310
0.8033	Intermediate Similarity	NPC474050
0.8033	Intermediate Similarity	NPC474114
0.8033	Intermediate Similarity	NPC473931
0.8031	Intermediate Similarity	NPC86900
0.8017	Intermediate Similarity	NPC228425
0.8016	Intermediate Similarity	NPC98305
0.8016	Intermediate Similarity	NPC259703
0.8016	Intermediate Similarity	NPC32322
0.8	Intermediate Similarity	NPC213730
0.8	Intermediate Similarity	NPC262936
0.8	Intermediate Similarity	NPC296683
0.8	Intermediate Similarity	NPC30491
0.7986	Intermediate Similarity	NPC148545
0.7984	Intermediate Similarity	NPC76308
0.7984	Intermediate Similarity	NPC325295
0.7984	Intermediate Similarity	NPC477213
0.797	Intermediate Similarity	NPC17843
0.797	Intermediate Similarity	NPC110609
0.797	Intermediate Similarity	NPC70622
0.797	Intermediate Similarity	NPC246693
0.797	Intermediate Similarity	NPC242358
0.797	Intermediate Similarity	NPC478190
0.7967	Intermediate Similarity	NPC322197
0.7966	Intermediate Similarity	NPC54765
0.7953	Intermediate Similarity	NPC253627
0.7953	Intermediate Similarity	NPC196976
0.7951	Intermediate Similarity	NPC296144
0.7951	Intermediate Similarity	NPC28784
0.7949	Intermediate Similarity	NPC323810
0.7941	Intermediate Similarity	NPC475957
0.7941	Intermediate Similarity	NPC305060
0.7939	Intermediate Similarity	NPC247250
0.7939	Intermediate Similarity	NPC473744
0.7939	Intermediate Similarity	NPC767
0.7939	Intermediate Similarity	NPC217431
0.7937	Intermediate Similarity	NPC7151
0.7937	Intermediate Similarity	NPC478121
0.7937	Intermediate Similarity	NPC473662
0.7937	Intermediate Similarity	NPC216297
0.7929	Intermediate Similarity	NPC245482
0.7929	Intermediate Similarity	NPC301751
0.7929	Intermediate Similarity	NPC474982
0.7929	Intermediate Similarity	NPC471906
0.7926	Intermediate Similarity	NPC283088
0.7923	Intermediate Similarity	NPC474945
0.7923	Intermediate Similarity	NPC476022
0.7923	Intermediate Similarity	NPC267846
0.7923	Intermediate Similarity	NPC71610
0.792	Intermediate Similarity	NPC63126
0.792	Intermediate Similarity	NPC184527
0.792	Intermediate Similarity	NPC469609
0.7914	Intermediate Similarity	NPC469520
0.7914	Intermediate Similarity	NPC474961
0.7913	Intermediate Similarity	NPC128723
0.791	Intermediate Similarity	NPC52407
0.791	Intermediate Similarity	NPC78307
0.7907	Intermediate Similarity	NPC152525
0.7907	Intermediate Similarity	NPC164014
0.7907	Intermediate Similarity	NPC74507
0.7907	Intermediate Similarity	NPC234890
0.7907	Intermediate Similarity	NPC68756
0.7895	Intermediate Similarity	NPC476847
0.7895	Intermediate Similarity	NPC93015
0.7895	Intermediate Similarity	NPC85342
0.7891	Intermediate Similarity	NPC121168
0.7891	Intermediate Similarity	NPC11250
0.7886	Intermediate Similarity	NPC120280
0.7881	Intermediate Similarity	NPC219286
0.7881	Intermediate Similarity	NPC99557
0.7881	Intermediate Similarity	NPC13495
0.7879	Intermediate Similarity	NPC99731
0.7879	Intermediate Similarity	NPC474998
0.7874	Intermediate Similarity	NPC241001
0.7869	Intermediate Similarity	NPC43525
0.7863	Intermediate Similarity	NPC266689
0.7863	Intermediate Similarity	NPC30501
0.7863	Intermediate Similarity	NPC169250
0.7863	Intermediate Similarity	NPC105157
0.7863	Intermediate Similarity	NPC23126
0.7863	Intermediate Similarity	NPC100067
0.7863	Intermediate Similarity	NPC477211
0.7863	Intermediate Similarity	NPC116513
0.7863	Intermediate Similarity	NPC190043
0.7863	Intermediate Similarity	NPC98254
0.7863	Intermediate Similarity	NPC319422
0.7863	Intermediate Similarity	NPC477212
0.7863	Intermediate Similarity	NPC103356
0.7863	Intermediate Similarity	NPC162612
0.7863	Intermediate Similarity	NPC477214
0.7863	Intermediate Similarity	NPC72158
0.7857	Intermediate Similarity	NPC151197
0.7857	Intermediate Similarity	NPC469644
0.7852	Intermediate Similarity	NPC282780
0.7852	Intermediate Similarity	NPC202225
0.7852	Intermediate Similarity	NPC166480
0.7851	Intermediate Similarity	NPC63345
0.7845	Intermediate Similarity	NPC294741
0.7842	Intermediate Similarity	NPC91019
0.7842	Intermediate Similarity	NPC106519
0.7842	Intermediate Similarity	NPC187843
0.784	Intermediate Similarity	NPC476266
0.7836	Intermediate Similarity	NPC165612
0.7833	Intermediate Similarity	NPC63698
0.7833	Intermediate Similarity	NPC61885
0.7829	Intermediate Similarity	NPC273683
0.7826	Intermediate Similarity	NPC260000
0.782	Intermediate Similarity	NPC245395
0.782	Intermediate Similarity	NPC469705
0.782	Intermediate Similarity	NPC136588
0.782	Intermediate Similarity	NPC147757
0.782	Intermediate Similarity	NPC470122
0.782	Intermediate Similarity	NPC199253
0.782	Intermediate Similarity	NPC17968
0.7817	Intermediate Similarity	NPC472134
0.7815	Intermediate Similarity	NPC271274
0.7812	Intermediate Similarity	NPC154696
0.7812	Intermediate Similarity	NPC472271
0.7812	Intermediate Similarity	NPC251259
0.781	Intermediate Similarity	NPC44960
0.781	Intermediate Similarity	NPC474110

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 NPC31936 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	252
0.1-0.2	863
0.2-0.3	1364
0.3-0.4	2621
0.4-0.5	2201
0.5-0.6	1192
0.6-0.7	589
0.7-0.8	68
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
0.7971	Intermediate Similarity	NPD3400	Discontinued
0.7759	Intermediate Similarity	NPD3020	Approved
0.771	Intermediate Similarity	NPD1470	Approved
0.7674	Intermediate Similarity	NPD1201	Approved
0.7656	Intermediate Similarity	NPD3019	Approved
0.7656	Intermediate Similarity	NPD2932	Approved
0.7652	Intermediate Similarity	NPD2859	Approved
0.7652	Intermediate Similarity	NPD2860	Approved
0.7576	Intermediate Similarity	NPD1164	Approved
0.7565	Intermediate Similarity	NPD2934	Approved
0.7565	Intermediate Similarity	NPD2933	Approved
0.7518	Intermediate Similarity	NPD6355	Discontinued
0.75	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1237	Approved
0.7442	Intermediate Similarity	NPD1651	Approved
0.7442	Intermediate Similarity	NPD4196	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD7635	Approved
0.7429	Intermediate Similarity	NPD5406	Approved
0.7429	Intermediate Similarity	NPD5408	Approved
0.7429	Intermediate Similarity	NPD5404	Approved
0.7429	Intermediate Similarity	NPD5405	Approved
0.7426	Intermediate Similarity	NPD6798	Discontinued
0.7379	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD4380	Phase 2
0.7357	Intermediate Similarity	NPD3299	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.735	Intermediate Similarity	NPD1809	Phase 2
0.7339	Intermediate Similarity	NPD3021	Approved
0.7339	Intermediate Similarity	NPD3022	Approved
0.7333	Intermediate Similarity	NPD846	Approved
0.7333	Intermediate Similarity	NPD940	Approved
0.7328	Intermediate Similarity	NPD845	Approved
0.7319	Intermediate Similarity	NPD4060	Phase 1
0.7319	Intermediate Similarity	NPD943	Approved
0.7317	Intermediate Similarity	NPD2342	Discontinued
0.731	Intermediate Similarity	NPD7390	Discontinued
0.7305	Intermediate Similarity	NPD2935	Discontinued
0.7299	Intermediate Similarity	NPD3764	Approved
0.7292	Intermediate Similarity	NPD6190	Approved
0.7273	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD1432	Clinical (unspecified phase)
0.7246	Intermediate Similarity	NPD6663	Approved
0.7246	Intermediate Similarity	NPD6405	Approved
0.7246	Intermediate Similarity	NPD6407	Approved
0.7244	Intermediate Similarity	NPD7159	Clinical (unspecified phase)
0.7239	Intermediate Similarity	NPD1283	Approved
0.7234	Intermediate Similarity	NPD1510	Phase 2
0.7234	Intermediate Similarity	NPD2799	Discontinued
0.7231	Intermediate Similarity	NPD3091	Approved
0.7222	Intermediate Similarity	NPD6124	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD405	Clinical (unspecified phase)
0.7206	Intermediate Similarity	NPD5736	Approved
0.7206	Intermediate Similarity	NPD2861	Phase 2
0.7197	Intermediate Similarity	NPD3023	Approved
0.7197	Intermediate Similarity	NPD3026	Approved
0.7188	Intermediate Similarity	NPD2629	Approved
0.7185	Intermediate Similarity	NPD3094	Phase 2
0.7176	Intermediate Similarity	NPD3025	Approved
0.7176	Intermediate Similarity	NPD3024	Approved
0.7174	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7164	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD3092	Approved
0.7133	Intermediate Similarity	NPD6002	Phase 3
0.7133	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6006	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6003	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD6004	Phase 3
0.7133	Intermediate Similarity	NPD6005	Phase 3
0.7122	Intermediate Similarity	NPD6233	Phase 2
0.7121	Intermediate Similarity	NPD5238	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD289	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD1242	Phase 1
0.7105	Intermediate Similarity	NPD8455	Phase 2
0.7105	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7103	Intermediate Similarity	NPD4628	Phase 3
0.7083	Intermediate Similarity	NPD9495	Approved
0.7083	Intermediate Similarity	NPD1549	Phase 2
0.7078	Intermediate Similarity	NPD7075	Discontinued
0.7071	Intermediate Similarity	NPD2979	Phase 3
0.7071	Intermediate Similarity	NPD1240	Approved
0.7063	Intermediate Similarity	NPD4750	Phase 3
0.7063	Intermediate Similarity	NPD4476	Approved
0.7063	Intermediate Similarity	NPD4477	Approved
0.7059	Intermediate Similarity	NPD844	Approved
0.7059	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD2313	Discontinued
0.704	Intermediate Similarity	NPD9265	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD4908	Phase 1
0.7027	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7015	Intermediate Similarity	NPD1535	Discovery
0.7015	Intermediate Similarity	NPD1281	Approved
0.7015	Intermediate Similarity	NPD1610	Phase 2
0.7014	Intermediate Similarity	NPD2344	Approved
0.7014	Intermediate Similarity	NPD2343	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD6007	Clinical (unspecified phase)
0.7007	Intermediate Similarity	NPD3300	Phase 2
0.7	Intermediate Similarity	NPD4062	Phase 3
0.7	Intermediate Similarity	NPD288	Approved
0.6993	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7033	Discontinued
0.6992	Remote Similarity	NPD3095	Discontinued
0.6992	Remote Similarity	NPD5700	Clinical (unspecified phase)
0.6992	Remote Similarity	NPD4589	Approved
0.6986	Remote Similarity	NPD7003	Approved
0.6986	Remote Similarity	NPD3750	Approved
0.6978	Remote Similarity	NPD3027	Phase 3
0.6977	Remote Similarity	NPD4869	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD1607	Approved
0.697	Remote Similarity	NPD9545	Approved
0.697	Remote Similarity	NPD5303	Approved
0.697	Remote Similarity	NPD1894	Discontinued
0.697	Remote Similarity	NPD5304	Approved
0.6966	Remote Similarity	NPD2424	Discontinued
0.6963	Remote Similarity	NPD1481	Phase 2
0.6957	Remote Similarity	NPD4208	Discontinued
0.694	Remote Similarity	NPD3847	Discontinued
0.6934	Remote Similarity	NPD4103	Phase 2
0.6934	Remote Similarity	NPD4104	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD2797	Approved
0.6929	Remote Similarity	NPD9380	Clinical (unspecified phase)
0.6929	Remote Similarity	NPD3268	Approved
0.6928	Remote Similarity	NPD37	Approved
0.6928	Remote Similarity	NPD6801	Discontinued
0.6912	Remote Similarity	NPD4659	Approved
0.6903	Remote Similarity	NPD7768	Phase 2
0.6894	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2798	Approved
0.688	Remote Similarity	NPD5048	Discontinued
0.6871	Remote Similarity	NPD8166	Discontinued
0.687	Remote Similarity	NPD255	Approved
0.687	Remote Similarity	NPD256	Approved
0.6866	Remote Similarity	NPD2286	Discontinued
0.6866	Remote Similarity	NPD4626	Approved
0.6859	Remote Similarity	NPD4381	Clinical (unspecified phase)
0.6849	Remote Similarity	NPD5958	Discontinued
0.6849	Remote Similarity	NPD4534	Discontinued
0.6846	Remote Similarity	NPD2228	Approved
0.6846	Remote Similarity	NPD2234	Approved
0.6846	Remote Similarity	NPD2229	Approved
0.6842	Remote Similarity	NPD1759	Phase 1
0.6842	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7458	Discontinued
0.6842	Remote Similarity	NPD1548	Phase 1
0.6838	Remote Similarity	NPD2562	Approved
0.6838	Remote Similarity	NPD1608	Approved
0.6838	Remote Similarity	NPD2561	Approved
0.6838	Remote Similarity	NPD3972	Approved
0.6835	Remote Similarity	NPD6959	Discontinued
0.6833	Remote Similarity	NPD688	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6831	Remote Similarity	NPD1613	Approved
0.6829	Remote Similarity	NPD3028	Approved
0.6828	Remote Similarity	NPD2796	Approved
0.6828	Remote Similarity	NPD2438	Suspended
0.6824	Remote Similarity	NPD2309	Approved
0.6824	Remote Similarity	NPD7910	Clinical (unspecified phase)
0.6818	Remote Similarity	NPD1934	Approved
0.6818	Remote Similarity	NPD7325	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6167	Clinical (unspecified phase)
0.6813	Remote Similarity	NPD6166	Phase 2
0.6813	Remote Similarity	NPD6168	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD1129	Approved
0.6812	Remote Similarity	NPD1134	Approved
0.6812	Remote Similarity	NPD1133	Approved
0.6812	Remote Similarity	NPD1131	Approved
0.6812	Remote Similarity	NPD1135	Approved
0.6806	Remote Similarity	NPD3552	Approved
0.6806	Remote Similarity	NPD3554	Approved
0.6806	Remote Similarity	NPD3555	Approved
0.6806	Remote Similarity	NPD4978	Clinical (unspecified phase)
0.6806	Remote Similarity	NPD3553	Approved
0.6803	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.68	Remote Similarity	NPD7410	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD3882	Suspended
0.6795	Remote Similarity	NPD4967	Phase 2
0.6795	Remote Similarity	NPD4965	Approved
0.6795	Remote Similarity	NPD4966	Approved
0.6794	Remote Similarity	NPD497	Approved
0.6794	Remote Similarity	NPD1476	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3787	Discontinued
0.6792	Remote Similarity	NPD6232	Discontinued
0.6788	Remote Similarity	NPD1755	Approved
0.6788	Remote Similarity	NPD4379	Clinical (unspecified phase)
0.6783	Remote Similarity	NPD111	Approved
0.6781	Remote Similarity	NPD2346	Discontinued
0.6781	Remote Similarity	NPD5762	Approved
0.6781	Remote Similarity	NPD5763	Approved
0.6779	Remote Similarity	NPD6666	Approved
0.6779	Remote Similarity	NPD6667	Approved
0.6774	Remote Similarity	NPD7819	Suspended
0.677	Remote Similarity	NPD7473	Discontinued
0.6767	Remote Similarity	NPD1758	Phase 1
0.6765	Remote Similarity	NPD1547	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD1878	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD1512	Approved
0.6753	Remote Similarity	NPD7411	Suspended

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