NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	452.18
Volume:	438.15
LogP:	2.843
LogD:	2.118
LogS:	-4.988
# Rotatable Bonds:	1
TPSA:	104.96
# H-Bond Aceptor:	7
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.628
Synthetic Accessibility Score:	6.821
Fsp3:	0.654
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.721
MDCK Permeability:	1.8648410332389176e-05
Pgp-inhibitor:	0.002
Pgp-substrate:	0.496
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.807
30% Bioavailability (F30%):	0.514

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.986
Plasma Protein Binding (PPB):	86.24824523925781%
Volume Distribution (VD):	1.382
Pgp-substrate:	13.391752243041992%

ADMET: Metabolism

CYP1A2-inhibitor:	0.007
CYP1A2-substrate:	0.973
CYP2C19-inhibitor:	0.02
CYP2C19-substrate:	0.192
CYP2C9-inhibitor:	0.169
CYP2C9-substrate:	0.024
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.047
CYP3A4-inhibitor:	0.577
CYP3A4-substrate:	0.789

ADMET: Excretion

Clearance (CL):	11.471
Half-life (T1/2):	0.587

ADMET: Toxicity

hERG Blockers:	0.094
Human Hepatotoxicity (H-HT):	0.549
Drug-inuced Liver Injury (DILI):	0.3
AMES Toxicity:	0.482
Rat Oral Acute Toxicity:	0.979
Maximum Recommended Daily Dose:	0.974
Skin Sensitization:	0.812
Carcinogencity:	0.951
Eye Corrosion:	0.003
Eye Irritation:	0.135
Respiratory Toxicity:	0.982

Download Data

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

Natural Product: NPC478072

Natural Product ID:	NPC478072
*Common Name:**	Trichirubine A
IUPAC Name:	(1S,2S,4S,6S,7R,9R,11R,12S,17R,21S)-7-(2-hydroxy-5-oxo-2H-furan-4-yl)-1,6,12,17-tetramethyl-3,10,15-trioxaheptacyclo[12.6.1.02,4.02,12.06,11.09,11.017,21]henicosa-13,18-dien-20-one
Synonyms:	Trichirubine A
Standard InCHIKey:	KCEMPVMLWXZZLR-ZCVPZFCJSA-N
Standard InCHI:	InChI=1S/C26H28O7/c1-21-6-5-15(27)24(4)19(21)14(30-11-21)9-23(3)25-16(32-25)8-13(12-7-18(28)31-20(12)29)22(25,2)10-17-26(23,24)33-17/h5-7,9,13,16-19,28H,8,10-11H2,1-4H3/t13-,16+,17-,18?,19-,21-,22-,23-,24-,25+,26-/m0/s1
SMILES:	C[C@@]12C[C@H]3[C@]4(O3)[C@]([C@@]15[C@H](O5)C[C@H]2C6=CC(OC6=O)O)(C=C7[C@@H]8[C@@]4(C(=O)C=C[C@]8(CO7)C)C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	10389151
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0001640] Naphthopyrans

*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
NPO29381	Trichilia rubescens	Species	Meliaceae	Eukaryota	leaves	Kibale National Park, Uganda	2000-2001	PMID[19299148]
NPO29381	Trichilia rubescens	Species	Meliaceae	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
Organism	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	IC50	=	0.3	ug/ml	PMID[19299148]

☑ 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 NPC478072 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	308
0.1-0.2	1794
0.2-0.3	5008
0.3-0.4	8061
0.4-0.5	13743
0.5-0.6	8443
0.6-0.7	4560
0.7-0.8	722
0.8-0.85	49
0.85-0.9	8
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8871	High Similarity	NPC470419
0.864	High Similarity	NPC470418
0.8605	High Similarity	NPC175186
0.8605	High Similarity	NPC470851
0.8538	High Similarity	NPC471170
0.8462	Intermediate Similarity	NPC104382
0.845	Intermediate Similarity	NPC287423
0.8385	Intermediate Similarity	NPC473620
0.8385	Intermediate Similarity	NPC470850
0.8346	Intermediate Similarity	NPC471234
0.8321	Intermediate Similarity	NPC48414
0.8321	Intermediate Similarity	NPC473593
0.8321	Intermediate Similarity	NPC5153
0.8308	Intermediate Similarity	NPC42399
0.8271	Intermediate Similarity	NPC469674
0.8254	Intermediate Similarity	NPC470420
0.8217	Intermediate Similarity	NPC204812
0.8217	Intermediate Similarity	NPC472768
0.8201	Intermediate Similarity	NPC471172
0.8182	Intermediate Similarity	NPC231529
0.8168	Intermediate Similarity	NPC305496
0.8154	Intermediate Similarity	NPC8369
0.8154	Intermediate Similarity	NPC32868
0.8154	Intermediate Similarity	NPC8374
0.8154	Intermediate Similarity	NPC241456
0.8143	Intermediate Similarity	NPC194854
0.8143	Intermediate Similarity	NPC48813
0.8106	Intermediate Similarity	NPC311534
0.8092	Intermediate Similarity	NPC293112
0.8085	Intermediate Similarity	NPC16729
0.8085	Intermediate Similarity	NPC475462
0.808	Intermediate Similarity	NPC312017
0.808	Intermediate Similarity	NPC9848
0.8077	Intermediate Similarity	NPC473979
0.8077	Intermediate Similarity	NPC469789
0.8062	Intermediate Similarity	NPC46570
0.806	Intermediate Similarity	NPC472769
0.8045	Intermediate Similarity	NPC472770
0.8031	Intermediate Similarity	NPC469684
0.803	Intermediate Similarity	NPC298841
0.8016	Intermediate Similarity	NPC238667
0.8016	Intermediate Similarity	NPC261330
0.8015	Intermediate Similarity	NPC81736
0.8015	Intermediate Similarity	NPC172154
0.8	Intermediate Similarity	NPC153700
0.8	Intermediate Similarity	NPC88326
0.8	Intermediate Similarity	NPC107493
0.7986	Intermediate Similarity	NPC25887
0.7985	Intermediate Similarity	NPC476852
0.7984	Intermediate Similarity	NPC143755
0.7984	Intermediate Similarity	NPC4548
0.7984	Intermediate Similarity	NPC42776
0.7969	Intermediate Similarity	NPC475913
0.7955	Intermediate Similarity	NPC225049
0.7941	Intermediate Similarity	NPC476823
0.7939	Intermediate Similarity	NPC11895
0.7926	Intermediate Similarity	NPC231240
0.7923	Intermediate Similarity	NPC67569
0.7923	Intermediate Similarity	NPC204731
0.7923	Intermediate Similarity	NPC310511
0.7923	Intermediate Similarity	NPC473256
0.7923	Intermediate Similarity	NPC470878
0.791	Intermediate Similarity	NPC221414
0.791	Intermediate Similarity	NPC476851
0.7907	Intermediate Similarity	NPC474179
0.7907	Intermediate Similarity	NPC475520
0.7907	Intermediate Similarity	NPC476960
0.7907	Intermediate Similarity	NPC475834
0.7895	Intermediate Similarity	NPC473253
0.7895	Intermediate Similarity	NPC471357
0.7895	Intermediate Similarity	NPC117702
0.7895	Intermediate Similarity	NPC146456
0.7895	Intermediate Similarity	NPC469757
0.7891	Intermediate Similarity	NPC474518
0.7872	Intermediate Similarity	NPC471171
0.7868	Intermediate Similarity	NPC469673
0.7868	Intermediate Similarity	NPC316915
0.7868	Intermediate Similarity	NPC88668
0.7863	Intermediate Similarity	NPC170538
0.7863	Intermediate Similarity	NPC287236
0.7863	Intermediate Similarity	NPC470265
0.7863	Intermediate Similarity	NPC23786
0.7863	Intermediate Similarity	NPC222688
0.7852	Intermediate Similarity	NPC220757
0.7852	Intermediate Similarity	NPC213634
0.7852	Intermediate Similarity	NPC476863
0.7852	Intermediate Similarity	NPC196921
0.7852	Intermediate Similarity	NPC476862
0.7846	Intermediate Similarity	NPC474370
0.7846	Intermediate Similarity	NPC474585
0.784	Intermediate Similarity	NPC130302
0.7836	Intermediate Similarity	NPC473888
0.7836	Intermediate Similarity	NPC245094
0.7836	Intermediate Similarity	NPC476859
0.7829	Intermediate Similarity	NPC471249
0.7829	Intermediate Similarity	NPC473720
0.782	Intermediate Similarity	NPC473635
0.782	Intermediate Similarity	NPC63186
0.7812	Intermediate Similarity	NPC469794
0.7812	Intermediate Similarity	NPC106228
0.7812	Intermediate Similarity	NPC138372
0.7812	Intermediate Similarity	NPC72772
0.781	Intermediate Similarity	NPC248703
0.7803	Intermediate Similarity	NPC120724
0.7803	Intermediate Similarity	NPC471392
0.7801	Intermediate Similarity	NPC470426
0.7795	Intermediate Similarity	NPC122056
0.7794	Intermediate Similarity	NPC34963
0.7794	Intermediate Similarity	NPC471855
0.7786	Intermediate Similarity	NPC476825
0.7778	Intermediate Similarity	NPC10823
0.7778	Intermediate Similarity	NPC469752
0.7778	Intermediate Similarity	NPC471352
0.7778	Intermediate Similarity	NPC470880
0.7778	Intermediate Similarity	NPC251866
0.7778	Intermediate Similarity	NPC70542
0.7778	Intermediate Similarity	NPC471360
0.7778	Intermediate Similarity	NPC86159
0.7778	Intermediate Similarity	NPC6108
0.7778	Intermediate Similarity	NPC469753
0.7778	Intermediate Similarity	NPC471358
0.7778	Intermediate Similarity	NPC469751
0.7778	Intermediate Similarity	NPC469755
0.7778	Intermediate Similarity	NPC9499
0.7778	Intermediate Similarity	NPC17896
0.7778	Intermediate Similarity	NPC284406
0.7778	Intermediate Similarity	NPC471361
0.7778	Intermediate Similarity	NPC219085
0.7778	Intermediate Similarity	NPC469754
0.7778	Intermediate Similarity	NPC35109
0.7778	Intermediate Similarity	NPC180079
0.7778	Intermediate Similarity	NPC471359
0.7778	Intermediate Similarity	NPC89514
0.7778	Intermediate Similarity	NPC197707
0.7769	Intermediate Similarity	NPC312536
0.7769	Intermediate Similarity	NPC61520
0.7769	Intermediate Similarity	NPC264954
0.7769	Intermediate Similarity	NPC473274
0.7769	Intermediate Similarity	NPC473270
0.7769	Intermediate Similarity	NPC472667
0.7769	Intermediate Similarity	NPC161065
0.7752	Intermediate Similarity	NPC13713
0.7752	Intermediate Similarity	NPC58662
0.7752	Intermediate Similarity	NPC239273
0.7744	Intermediate Similarity	NPC469790
0.7737	Intermediate Similarity	NPC327664
0.7737	Intermediate Similarity	NPC58029
0.7737	Intermediate Similarity	NPC470427
0.7737	Intermediate Similarity	NPC476097
0.7734	Intermediate Similarity	NPC474181
0.7734	Intermediate Similarity	NPC470953
0.7727	Intermediate Similarity	NPC269642
0.7721	Intermediate Similarity	NPC475389
0.7721	Intermediate Similarity	NPC473838
0.7721	Intermediate Similarity	NPC241935
0.7721	Intermediate Similarity	NPC476855
0.7721	Intermediate Similarity	NPC173347
0.7721	Intermediate Similarity	NPC279478
0.7717	Intermediate Similarity	NPC12046
0.7717	Intermediate Similarity	NPC194951
0.7714	Intermediate Similarity	NPC75616
0.771	Intermediate Similarity	NPC241192
0.771	Intermediate Similarity	NPC79579
0.771	Intermediate Similarity	NPC257610
0.771	Intermediate Similarity	NPC472004
0.771	Intermediate Similarity	NPC476962
0.771	Intermediate Similarity	NPC48692
0.7698	Intermediate Similarity	NPC289700
0.7698	Intermediate Similarity	NPC124053
0.7698	Intermediate Similarity	NPC235014
0.7698	Intermediate Similarity	NPC68282
0.7698	Intermediate Similarity	NPC253906
0.7698	Intermediate Similarity	NPC59288
0.7698	Intermediate Similarity	NPC62172
0.7698	Intermediate Similarity	NPC179642
0.7692	Intermediate Similarity	NPC475372
0.7692	Intermediate Similarity	NPC153440
0.7692	Intermediate Similarity	NPC240509
0.7692	Intermediate Similarity	NPC284707
0.7692	Intermediate Similarity	NPC709
0.7692	Intermediate Similarity	NPC50774
0.7692	Intermediate Similarity	NPC329736
0.7692	Intermediate Similarity	NPC186525
0.7692	Intermediate Similarity	NPC113448
0.7687	Intermediate Similarity	NPC174367
0.7687	Intermediate Similarity	NPC47113
0.7681	Intermediate Similarity	NPC192334
0.7681	Intermediate Similarity	NPC60150
0.7674	Intermediate Similarity	NPC190286
0.7674	Intermediate Similarity	NPC268213
0.7674	Intermediate Similarity	NPC49492
0.7674	Intermediate Similarity	NPC266728
0.7674	Intermediate Similarity	NPC302471
0.7674	Intermediate Similarity	NPC148458
0.7674	Intermediate Similarity	NPC470793
0.7669	Intermediate Similarity	NPC27363
0.7669	Intermediate Similarity	NPC55602
0.7669	Intermediate Similarity	NPC469382
0.7664	Intermediate Similarity	NPC42206
0.7664	Intermediate Similarity	NPC476824

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 NPC478072 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	2027
0.2-0.3	3867
0.3-0.4	2003
0.4-0.5	595
0.5-0.6	232
0.6-0.7	144
0.7-0.8	19
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
0.7805	Intermediate Similarity	NPD6008	Approved
0.7778	Intermediate Similarity	NPD7319	Approved
0.7727	Intermediate Similarity	NPD6370	Approved
0.7704	Intermediate Similarity	NPD7736	Approved
0.763	Intermediate Similarity	NPD7078	Approved
0.7615	Intermediate Similarity	NPD7115	Discovery
0.7612	Intermediate Similarity	NPD7492	Approved
0.7576	Intermediate Similarity	NPD6054	Approved
0.7556	Intermediate Similarity	NPD6616	Approved
0.7556	Intermediate Similarity	NPD7507	Approved
0.7519	Intermediate Similarity	NPD6015	Approved
0.7519	Intermediate Similarity	NPD6016	Approved
0.75	Intermediate Similarity	NPD8293	Discontinued
0.7463	Intermediate Similarity	NPD5988	Approved
0.7344	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7323	Intermediate Similarity	NPD5697	Approved
0.7313	Intermediate Similarity	NPD6319	Approved
0.7313	Intermediate Similarity	NPD6059	Approved
0.7308	Intermediate Similarity	NPD6053	Discontinued
0.7308	Intermediate Similarity	NPD6882	Approved
0.7293	Intermediate Similarity	NPD7328	Approved
0.7293	Intermediate Similarity	NPD7327	Approved
0.7287	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7266	Intermediate Similarity	NPD6899	Approved
0.7266	Intermediate Similarity	NPD6881	Approved
0.7239	Intermediate Similarity	NPD7516	Approved
0.7231	Intermediate Similarity	NPD6649	Approved
0.7231	Intermediate Similarity	NPD6650	Approved
0.7218	Intermediate Similarity	NPD6009	Approved
0.7209	Intermediate Similarity	NPD6013	Approved
0.7209	Intermediate Similarity	NPD6014	Approved
0.7209	Intermediate Similarity	NPD6012	Approved
0.7188	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD6883	Approved
0.7154	Intermediate Similarity	NPD7102	Approved
0.7154	Intermediate Similarity	NPD7290	Approved
0.7143	Intermediate Similarity	NPD5211	Phase 2
0.7132	Intermediate Similarity	NPD7503	Approved
0.7132	Intermediate Similarity	NPD6011	Approved
0.7132	Intermediate Similarity	NPD7320	Approved
0.7121	Intermediate Similarity	NPD4632	Approved
0.7109	Intermediate Similarity	NPD6675	Approved
0.7109	Intermediate Similarity	NPD7128	Approved
0.7109	Intermediate Similarity	NPD5739	Approved
0.7109	Intermediate Similarity	NPD6402	Approved
0.7099	Intermediate Similarity	NPD8130	Phase 1
0.7099	Intermediate Similarity	NPD6869	Approved
0.7099	Intermediate Similarity	NPD6847	Approved
0.7099	Intermediate Similarity	NPD6617	Approved
0.7077	Intermediate Similarity	NPD6373	Approved
0.7077	Intermediate Similarity	NPD6372	Approved
0.7054	Intermediate Similarity	NPD5701	Approved
0.7045	Intermediate Similarity	NPD8297	Approved
0.7031	Intermediate Similarity	NPD5141	Approved
0.7023	Intermediate Similarity	NPD4634	Approved
0.7007	Intermediate Similarity	NPD8296	Approved
0.7007	Intermediate Similarity	NPD8380	Approved
0.7007	Intermediate Similarity	NPD8379	Approved
0.7007	Intermediate Similarity	NPD8033	Approved
0.7007	Intermediate Similarity	NPD8335	Approved
0.7007	Intermediate Similarity	NPD8378	Approved
0.6984	Remote Similarity	NPD5285	Approved
0.6984	Remote Similarity	NPD4696	Approved
0.6984	Remote Similarity	NPD7640	Approved
0.6984	Remote Similarity	NPD7639	Approved
0.6984	Remote Similarity	NPD5286	Approved
0.6934	Remote Similarity	NPD8294	Approved
0.6934	Remote Similarity	NPD8377	Approved
0.6906	Remote Similarity	NPD7604	Phase 2
0.6905	Remote Similarity	NPD7638	Approved
0.6884	Remote Similarity	NPD8513	Phase 3
0.6884	Remote Similarity	NPD8516	Approved
0.6884	Remote Similarity	NPD5983	Phase 2
0.6884	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD8515	Approved
0.6884	Remote Similarity	NPD8517	Approved
0.6875	Remote Similarity	NPD5224	Approved
0.6875	Remote Similarity	NPD4633	Approved
0.6875	Remote Similarity	NPD5225	Approved
0.6875	Remote Similarity	NPD5226	Approved
0.687	Remote Similarity	NPD6686	Approved
0.6831	Remote Similarity	NPD6033	Approved
0.6825	Remote Similarity	NPD4755	Approved
0.6822	Remote Similarity	NPD5174	Approved
0.6822	Remote Similarity	NPD5175	Approved
0.68	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6797	Remote Similarity	NPD5223	Approved
0.6797	Remote Similarity	NPD5344	Discontinued
0.6794	Remote Similarity	NPD6412	Phase 2
0.6772	Remote Similarity	NPD4225	Approved
0.6767	Remote Similarity	NPD6371	Approved
0.6765	Remote Similarity	NPD6274	Approved
0.6742	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6739	Remote Similarity	NPD7101	Approved
0.6739	Remote Similarity	NPD7100	Approved
0.672	Remote Similarity	NPD6001	Approved
0.6719	Remote Similarity	NPD4700	Approved
0.6719	Remote Similarity	NPD6648	Approved
0.6716	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6317	Approved
0.669	Remote Similarity	NPD6336	Discontinued
0.6667	Remote Similarity	NPD6335	Approved
0.6667	Remote Similarity	NPD6313	Approved
0.6667	Remote Similarity	NPD5695	Phase 3
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD8328	Phase 3
0.6667	Remote Similarity	NPD6314	Approved
0.6617	Remote Similarity	NPD4730	Approved
0.6617	Remote Similarity	NPD4729	Approved
0.6613	Remote Similarity	NPD5207	Approved
0.6613	Remote Similarity	NPD5785	Approved
0.6562	Remote Similarity	NPD6084	Phase 2
0.6562	Remote Similarity	NPD6083	Phase 2
0.656	Remote Similarity	NPD5281	Approved
0.656	Remote Similarity	NPD5284	Approved
0.656	Remote Similarity	NPD6079	Approved
0.6549	Remote Similarity	NPD6067	Discontinued
0.6533	Remote Similarity	NPD6333	Approved
0.6533	Remote Similarity	NPD6334	Approved
0.6519	Remote Similarity	NPD5248	Approved
0.6519	Remote Similarity	NPD5249	Phase 3
0.6519	Remote Similarity	NPD5247	Approved
0.6519	Remote Similarity	NPD5250	Approved
0.6519	Remote Similarity	NPD5251	Approved
0.6512	Remote Similarity	NPD5696	Approved
0.6508	Remote Similarity	NPD5779	Approved
0.6508	Remote Similarity	NPD5778	Approved
0.6508	Remote Similarity	NPD4202	Approved
0.6508	Remote Similarity	NPD6399	Phase 3
0.6507	Remote Similarity	NPD5956	Approved
0.6493	Remote Similarity	NPD5128	Approved
0.6489	Remote Similarity	NPD7632	Discontinued
0.6484	Remote Similarity	NPD5222	Approved
0.6484	Remote Similarity	NPD5221	Approved
0.6484	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6475	Remote Similarity	NPD1694	Approved
0.6471	Remote Similarity	NPD5215	Approved
0.6471	Remote Similarity	NPD5217	Approved
0.6471	Remote Similarity	NPD5216	Approved
0.6466	Remote Similarity	NPD4768	Approved
0.6466	Remote Similarity	NPD4767	Approved
0.6463	Remote Similarity	NPD7260	Phase 2
0.6457	Remote Similarity	NPD5282	Discontinued
0.6439	Remote Similarity	NPD4754	Approved
0.6434	Remote Similarity	NPD5173	Approved
0.6429	Remote Similarity	NPD5693	Phase 1
0.6418	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6414	Remote Similarity	NPD8074	Phase 3
0.6412	Remote Similarity	NPD1700	Approved
0.6412	Remote Similarity	NPD7799	Discontinued
0.6408	Remote Similarity	NPD6908	Approved
0.6408	Remote Similarity	NPD6909	Approved
0.6406	Remote Similarity	NPD5210	Approved
0.6406	Remote Similarity	NPD4629	Approved
0.64	Remote Similarity	NPD5328	Approved
0.64	Remote Similarity	NPD1695	Approved
0.6397	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD5169	Approved
0.6397	Remote Similarity	NPD5135	Approved
0.6377	Remote Similarity	NPD8133	Approved
0.6357	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6357	Remote Similarity	NPD4697	Phase 3
0.635	Remote Similarity	NPD5127	Approved
0.6341	Remote Similarity	NPD5760	Phase 2
0.6341	Remote Similarity	NPD5761	Phase 2
0.6324	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.632	Remote Similarity	NPD6903	Approved
0.6309	Remote Similarity	NPD6845	Suspended
0.6309	Remote Similarity	NPD8338	Approved
0.6299	Remote Similarity	NPD6411	Approved
0.6299	Remote Similarity	NPD5694	Approved
0.6299	Remote Similarity	NPD7637	Suspended
0.629	Remote Similarity	NPD7521	Approved
0.629	Remote Similarity	NPD6409	Approved
0.629	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.629	Remote Similarity	NPD5330	Approved
0.629	Remote Similarity	NPD4249	Approved
0.629	Remote Similarity	NPD6684	Approved
0.629	Remote Similarity	NPD7146	Approved
0.629	Remote Similarity	NPD3618	Phase 1
0.629	Remote Similarity	NPD7334	Approved
0.6286	Remote Similarity	NPD6868	Approved
0.627	Remote Similarity	NPD4753	Phase 2
0.624	Remote Similarity	NPD4250	Approved
0.624	Remote Similarity	NPD4251	Approved
0.624	Remote Similarity	NPD3573	Approved
0.622	Remote Similarity	NPD5692	Phase 3
0.6214	Remote Similarity	NPD5167	Approved
0.621	Remote Similarity	NPD5363	Approved
0.619	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6183	Remote Similarity	NPD7902	Approved
0.6181	Remote Similarity	NPD6921	Approved
0.6172	Remote Similarity	NPD6050	Approved
0.616	Remote Similarity	NPD5690	Phase 2
0.616	Remote Similarity	NPD5786	Approved
0.6142	Remote Similarity	NPD6101	Approved
0.6142	Remote Similarity	NPD6673	Approved
0.6142	Remote Similarity	NPD6904	Approved
0.6142	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6142	Remote Similarity	NPD6080	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