NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	440.33
Volume:	491.739
LogP:	7.116
LogD:	5.679
LogS:	-6.982
# Rotatable Bonds:	3
TPSA:	35.53
# H-Bond Aceptor:	3
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.434
Synthetic Accessibility Score:	5.502
Fsp3:	0.759
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.815
MDCK Permeability:	1.0896768799284473e-05
Pgp-inhibitor:	0.997
Pgp-substrate:	0.004
Human Intestinal Absorption (HIA):	0.007
20% Bioavailability (F20%):	0.962
30% Bioavailability (F30%):	0.966

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.029
Plasma Protein Binding (PPB):	97.47570037841797%
Volume Distribution (VD):	2.564
Pgp-substrate:	2.8605074882507324%

ADMET: Metabolism

CYP1A2-inhibitor:	0.18
CYP1A2-substrate:	0.526
CYP2C19-inhibitor:	0.816
CYP2C19-substrate:	0.922
CYP2C9-inhibitor:	0.928
CYP2C9-substrate:	0.044
CYP2D6-inhibitor:	0.865
CYP2D6-substrate:	0.03
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.903

ADMET: Excretion

Clearance (CL):	3.726
Half-life (T1/2):	0.046

ADMET: Toxicity

hERG Blockers:	0.021
Human Hepatotoxicity (H-HT):	0.258
Drug-inuced Liver Injury (DILI):	0.907
AMES Toxicity:	0.015
Rat Oral Acute Toxicity:	0.418
Maximum Recommended Daily Dose:	0.166
Skin Sensitization:	0.17
Carcinogencity:	0.147
Eye Corrosion:	0.004
Eye Irritation:	0.023
Respiratory Toxicity:	0.95

Download Data

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

Natural Product: NPC478259

Natural Product ID:	NPC478259
*Common Name:**	Frutescone I
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	VBRJBFPGRNHVMG-LGPUIHHESA-N
Standard InCHI:	InChI=1S/C29H44O3/c1-16(2)20-11-10-18(5)21-12-13-29(15-23(20)21)14-22(17(3)4)24-25(30)19(6)26(31-9)28(7,8)27(24)32-29/h15-18,20-22H,10-14H2,1-9H3/t18-,20+,21-,22-,29-/m1/s1
SMILES:	[H][C@]12CC[C@]3(C=C1[C@H](C(C)C)CC[C@H]2C)C[C@H](C(C)C)C1=C(O3)C(C)(C)C(OC)=C(C)C1=O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001550] Sesquiterpenoids

*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
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	leaf	n.a.	DOI[10.1016/S0031-9422(98)00534-2]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12932146]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	aerial parts	Nanning, Guangxi Province, China	2014-OCT	PMID[28753309]
NPO11277	Baeckea frutescens	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO11277	Baeckea frutescens	Species	Myrtaceae	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

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

☑ 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 NPC478259 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	223
0.1-0.2	1463
0.2-0.3	4571
0.3-0.4	10761
0.4-0.5	14368
0.5-0.6	7479
0.6-0.7	3490
0.7-0.8	332
0.8-0.85	10
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC478261
1.0	High Similarity	NPC478260
0.8444	Intermediate Similarity	NPC253177
0.8444	Intermediate Similarity	NPC280592
0.8444	Intermediate Similarity	NPC213636
0.8352	Intermediate Similarity	NPC296114
0.8352	Intermediate Similarity	NPC471329
0.8295	Intermediate Similarity	NPC478245
0.8242	Intermediate Similarity	NPC223093
0.8202	Intermediate Similarity	NPC220478
0.809	Intermediate Similarity	NPC133652
0.8046	Intermediate Similarity	NPC478262
0.8046	Intermediate Similarity	NPC474085
0.7957	Intermediate Similarity	NPC190442
0.7935	Intermediate Similarity	NPC284561
0.7907	Intermediate Similarity	NPC478246
0.7907	Intermediate Similarity	NPC478247
0.79	Intermediate Similarity	NPC478052
0.7889	Intermediate Similarity	NPC137493
0.7872	Intermediate Similarity	NPC229976
0.7857	Intermediate Similarity	NPC472637
0.7857	Intermediate Similarity	NPC310981
0.7849	Intermediate Similarity	NPC478258
0.7849	Intermediate Similarity	NPC478257
0.7826	Intermediate Similarity	NPC143025
0.7826	Intermediate Similarity	NPC472302
0.7802	Intermediate Similarity	NPC470345
0.7766	Intermediate Similarity	NPC472975
0.7723	Intermediate Similarity	NPC60681
0.7717	Intermediate Similarity	NPC471728
0.7717	Intermediate Similarity	NPC477228
0.7708	Intermediate Similarity	NPC127197
0.7701	Intermediate Similarity	NPC469996
0.77	Intermediate Similarity	NPC470954
0.7692	Intermediate Similarity	NPC470048
0.7692	Intermediate Similarity	NPC263997
0.7692	Intermediate Similarity	NPC8518
0.7692	Intermediate Similarity	NPC189311
0.7692	Intermediate Similarity	NPC132228
0.7667	Intermediate Similarity	NPC470046
0.7667	Intermediate Similarity	NPC193198
0.7667	Intermediate Similarity	NPC470047
0.766	Intermediate Similarity	NPC113393
0.766	Intermediate Similarity	NPC469595
0.766	Intermediate Similarity	NPC220454
0.766	Intermediate Similarity	NPC212679
0.766	Intermediate Similarity	NPC476369
0.766	Intermediate Similarity	NPC476437
0.7609	Intermediate Similarity	NPC470051
0.7609	Intermediate Similarity	NPC470050
0.7604	Intermediate Similarity	NPC476415
0.76	Intermediate Similarity	NPC185530
0.7596	Intermediate Similarity	NPC37116
0.7596	Intermediate Similarity	NPC473627
0.7586	Intermediate Similarity	NPC472300
0.7582	Intermediate Similarity	NPC476412
0.7573	Intermediate Similarity	NPC177064
0.7558	Intermediate Similarity	NPC65650
0.7553	Intermediate Similarity	NPC173042
0.7553	Intermediate Similarity	NPC280833
0.7551	Intermediate Similarity	NPC84335
0.7551	Intermediate Similarity	NPC38530
0.7551	Intermediate Similarity	NPC151488
0.7528	Intermediate Similarity	NPC108955
0.7528	Intermediate Similarity	NPC2482
0.7527	Intermediate Similarity	NPC38885
0.7527	Intermediate Similarity	NPC30421
0.7526	Intermediate Similarity	NPC472932
0.7526	Intermediate Similarity	NPC316215
0.7525	Intermediate Similarity	NPC26478
0.75	Intermediate Similarity	NPC275494
0.75	Intermediate Similarity	NPC241512
0.75	Intermediate Similarity	NPC6185
0.75	Intermediate Similarity	NPC474899
0.75	Intermediate Similarity	NPC472930
0.75	Intermediate Similarity	NPC471409
0.75	Intermediate Similarity	NPC474912
0.75	Intermediate Similarity	NPC476678
0.7476	Intermediate Similarity	NPC91034
0.7475	Intermediate Similarity	NPC176845
0.7474	Intermediate Similarity	NPC152467
0.7474	Intermediate Similarity	NPC469372
0.7474	Intermediate Similarity	NPC273199
0.7474	Intermediate Similarity	NPC159748
0.7474	Intermediate Similarity	NPC212369
0.7474	Intermediate Similarity	NPC101651
0.7474	Intermediate Similarity	NPC38952
0.7473	Intermediate Similarity	NPC288281
0.7473	Intermediate Similarity	NPC22611
0.7473	Intermediate Similarity	NPC53733
0.7453	Intermediate Similarity	NPC221144
0.7451	Intermediate Similarity	NPC476001
0.7451	Intermediate Similarity	NPC474898
0.7449	Intermediate Similarity	NPC472733
0.7449	Intermediate Similarity	NPC472734
0.7447	Intermediate Similarity	NPC24816
0.7447	Intermediate Similarity	NPC307298
0.7444	Intermediate Similarity	NPC55869
0.7429	Intermediate Similarity	NPC29133
0.7426	Intermediate Similarity	NPC475320
0.7423	Intermediate Similarity	NPC470697
0.7423	Intermediate Similarity	NPC38830
0.7419	Intermediate Similarity	NPC472974
0.7416	Intermediate Similarity	NPC476177
0.74	Intermediate Similarity	NPC54705
0.74	Intermediate Similarity	NPC476933
0.7396	Intermediate Similarity	NPC478243
0.7396	Intermediate Similarity	NPC472978
0.7396	Intermediate Similarity	NPC303697
0.7396	Intermediate Similarity	NPC218301
0.7396	Intermediate Similarity	NPC478244
0.7391	Intermediate Similarity	NPC30486
0.7391	Intermediate Similarity	NPC312660
0.7374	Intermediate Similarity	NPC170131
0.7374	Intermediate Similarity	NPC472731
0.7374	Intermediate Similarity	NPC472732
0.7374	Intermediate Similarity	NPC76266
0.7368	Intermediate Similarity	NPC5509
0.7368	Intermediate Similarity	NPC472973
0.7363	Intermediate Similarity	NPC327969
0.7363	Intermediate Similarity	NPC321289
0.7363	Intermediate Similarity	NPC186276
0.7358	Intermediate Similarity	NPC470961
0.7353	Intermediate Similarity	NPC132395
0.7353	Intermediate Similarity	NPC111323
0.7353	Intermediate Similarity	NPC179208
0.7353	Intermediate Similarity	NPC254202
0.7353	Intermediate Similarity	NPC471365
0.7353	Intermediate Similarity	NPC471364
0.7347	Intermediate Similarity	NPC259286
0.7347	Intermediate Similarity	NPC171395
0.7347	Intermediate Similarity	NPC295347
0.7347	Intermediate Similarity	NPC33473
0.734	Intermediate Similarity	NPC231599
0.734	Intermediate Similarity	NPC113370
0.734	Intermediate Similarity	NPC181327
0.734	Intermediate Similarity	NPC103743
0.734	Intermediate Similarity	NPC476079
0.734	Intermediate Similarity	NPC171722
0.7333	Intermediate Similarity	NPC267517
0.7333	Intermediate Similarity	NPC195424
0.7333	Intermediate Similarity	NPC137911
0.7333	Intermediate Similarity	NPC228477
0.7327	Intermediate Similarity	NPC476888
0.7327	Intermediate Similarity	NPC93744
0.7327	Intermediate Similarity	NPC194028
0.7327	Intermediate Similarity	NPC168319
0.732	Intermediate Similarity	NPC263780
0.732	Intermediate Similarity	NPC69454
0.732	Intermediate Similarity	NPC169343
0.732	Intermediate Similarity	NPC476416
0.732	Intermediate Similarity	NPC271652
0.732	Intermediate Similarity	NPC1108
0.7315	Intermediate Similarity	NPC474181
0.7312	Intermediate Similarity	NPC110405
0.7312	Intermediate Similarity	NPC2709
0.7312	Intermediate Similarity	NPC469948
0.7308	Intermediate Similarity	NPC144459
0.7308	Intermediate Similarity	NPC475294
0.7308	Intermediate Similarity	NPC476958
0.7303	Intermediate Similarity	NPC470052
0.7303	Intermediate Similarity	NPC471220
0.7303	Intermediate Similarity	NPC189485
0.7303	Intermediate Similarity	NPC4827
0.73	Intermediate Similarity	NPC472730
0.73	Intermediate Similarity	NPC153776
0.73	Intermediate Similarity	NPC177680
0.73	Intermediate Similarity	NPC478056
0.73	Intermediate Similarity	NPC472729
0.7292	Intermediate Similarity	NPC328141
0.7292	Intermediate Similarity	NPC8062
0.7292	Intermediate Similarity	NPC198818
0.7292	Intermediate Similarity	NPC76286
0.729	Intermediate Similarity	NPC191620
0.7283	Intermediate Similarity	NPC64600
0.7282	Intermediate Similarity	NPC40170
0.7282	Intermediate Similarity	NPC189616
0.7273	Intermediate Similarity	NPC249954
0.7273	Intermediate Similarity	NPC472305
0.7273	Intermediate Similarity	NPC92080
0.7273	Intermediate Similarity	NPC29952
0.7273	Intermediate Similarity	NPC112654
0.7273	Intermediate Similarity	NPC40353
0.7273	Intermediate Similarity	NPC328371
0.7273	Intermediate Similarity	NPC153440
0.7273	Intermediate Similarity	NPC899
0.7263	Intermediate Similarity	NPC470524
0.7263	Intermediate Similarity	NPC215831
0.7263	Intermediate Similarity	NPC226863
0.7255	Intermediate Similarity	NPC80781
0.7255	Intermediate Similarity	NPC40918
0.7255	Intermediate Similarity	NPC476890
0.7253	Intermediate Similarity	NPC44963
0.7253	Intermediate Similarity	NPC282293
0.7253	Intermediate Similarity	NPC471898
0.7253	Intermediate Similarity	NPC472684
0.7253	Intermediate Similarity	NPC149237
0.7253	Intermediate Similarity	NPC225515
0.7253	Intermediate Similarity	NPC121984
0.7253	Intermediate Similarity	NPC99308

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 NPC478259 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	212
0.1-0.2	1665
0.2-0.3	3823
0.3-0.4	2314
0.4-0.5	779
0.5-0.6	201
0.6-0.7	153
0.7-0.8	3
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
0.7527	Intermediate Similarity	NPD3573	Approved
0.7263	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD7334	Approved
0.7234	Intermediate Similarity	NPD5330	Approved
0.7234	Intermediate Similarity	NPD6409	Approved
0.7234	Intermediate Similarity	NPD7146	Approved
0.7234	Intermediate Similarity	NPD6684	Approved
0.7234	Intermediate Similarity	NPD7521	Approved
0.7216	Intermediate Similarity	NPD5693	Phase 1
0.7174	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4695	Discontinued
0.713	Intermediate Similarity	NPD6053	Discontinued
0.7083	Intermediate Similarity	NPD5737	Approved
0.7083	Intermediate Similarity	NPD6672	Approved
0.7083	Intermediate Similarity	NPD6903	Approved
0.7053	Intermediate Similarity	NPD4623	Approved
0.7053	Intermediate Similarity	NPD4519	Discontinued
0.7041	Intermediate Similarity	NPD6050	Approved
0.701	Intermediate Similarity	NPD6673	Approved
0.701	Intermediate Similarity	NPD6904	Approved
0.701	Intermediate Similarity	NPD5328	Approved
0.701	Intermediate Similarity	NPD6080	Approved
0.701	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5695	Phase 3
0.6989	Remote Similarity	NPD4221	Approved
0.6989	Remote Similarity	NPD4223	Phase 3
0.6947	Remote Similarity	NPD1694	Approved
0.6947	Remote Similarity	NPD5329	Approved
0.6939	Remote Similarity	NPD5692	Phase 3
0.6939	Remote Similarity	NPD5207	Approved
0.6907	Remote Similarity	NPD5208	Approved
0.69	Remote Similarity	NPD7748	Approved
0.69	Remote Similarity	NPD7900	Approved
0.69	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD5280	Approved
0.6875	Remote Similarity	NPD5690	Phase 2
0.6875	Remote Similarity	NPD6098	Approved
0.6875	Remote Similarity	NPD4694	Approved
0.6875	Remote Similarity	NPD7115	Discovery
0.6869	Remote Similarity	NPD5694	Approved
0.6869	Remote Similarity	NPD6079	Approved
0.6863	Remote Similarity	NPD6083	Phase 2
0.6863	Remote Similarity	NPD6084	Phase 2
0.6854	Remote Similarity	NPD5733	Approved
0.6842	Remote Similarity	NPD3666	Approved
0.6842	Remote Similarity	NPD3665	Phase 1
0.6842	Remote Similarity	NPD3133	Approved
0.6842	Remote Similarity	NPD4786	Approved
0.6842	Remote Similarity	NPD4197	Approved
0.6837	Remote Similarity	NPD4753	Phase 2
0.6832	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7331	Phase 2
0.6809	Remote Similarity	NPD3667	Approved
0.6782	Remote Similarity	NPD4137	Phase 3
0.6765	Remote Similarity	NPD7732	Phase 3
0.6739	Remote Similarity	NPD3617	Approved
0.6729	Remote Similarity	NPD6402	Approved
0.6729	Remote Similarity	NPD7128	Approved
0.6729	Remote Similarity	NPD5739	Approved
0.6729	Remote Similarity	NPD6675	Approved
0.6706	Remote Similarity	NPD7341	Phase 2
0.6705	Remote Similarity	NPD4747	Approved
0.6705	Remote Similarity	NPD4691	Approved
0.6701	Remote Similarity	NPD4689	Approved
0.6701	Remote Similarity	NPD4693	Phase 3
0.6701	Remote Similarity	NPD5205	Approved
0.6701	Remote Similarity	NPD5279	Phase 3
0.6701	Remote Similarity	NPD3618	Phase 1
0.6701	Remote Similarity	NPD4690	Approved
0.6701	Remote Similarity	NPD4688	Approved
0.6701	Remote Similarity	NPD4138	Approved
0.67	Remote Similarity	NPD6411	Approved
0.67	Remote Similarity	NPD7515	Phase 2
0.6699	Remote Similarity	NPD7902	Approved
0.6699	Remote Similarity	NPD4755	Approved
0.6667	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6101	Approved
0.6667	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD3668	Phase 3
0.6635	Remote Similarity	NPD5696	Approved
0.6634	Remote Similarity	NPD6399	Phase 3
0.6634	Remote Similarity	NPD5778	Approved
0.6634	Remote Similarity	NPD5779	Approved
0.6629	Remote Similarity	NPD5276	Approved
0.6606	Remote Similarity	NPD7320	Approved
0.6606	Remote Similarity	NPD6899	Approved
0.6606	Remote Similarity	NPD6881	Approved
0.6604	Remote Similarity	NPD5211	Phase 2
0.6593	Remote Similarity	NPD8039	Approved
0.6574	Remote Similarity	NPD6008	Approved
0.6571	Remote Similarity	NPD5286	Approved
0.6571	Remote Similarity	NPD4700	Approved
0.6571	Remote Similarity	NPD4696	Approved
0.6571	Remote Similarity	NPD5285	Approved
0.6569	Remote Similarity	NPD6001	Approved
0.6545	Remote Similarity	NPD6373	Approved
0.6545	Remote Similarity	NPD6372	Approved
0.6535	Remote Similarity	NPD5284	Approved
0.6535	Remote Similarity	NPD5281	Approved
0.6531	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD5697	Approved
0.6514	Remote Similarity	NPD5701	Approved
0.6505	Remote Similarity	NPD4629	Approved
0.6505	Remote Similarity	NPD5210	Approved
0.6505	Remote Similarity	NPD5654	Approved
0.65	Remote Similarity	NPD6051	Approved
0.6486	Remote Similarity	NPD7102	Approved
0.6486	Remote Similarity	NPD7290	Approved
0.6486	Remote Similarity	NPD6883	Approved
0.6484	Remote Similarity	NPD4058	Approved
0.6481	Remote Similarity	NPD5141	Approved
0.6476	Remote Similarity	NPD7638	Approved
0.6471	Remote Similarity	NPD4202	Approved
0.6449	Remote Similarity	NPD5225	Approved
0.6449	Remote Similarity	NPD5224	Approved
0.6449	Remote Similarity	NPD5226	Approved
0.6449	Remote Similarity	NPD4633	Approved
0.6442	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD4697	Phase 3
0.6442	Remote Similarity	NPD5221	Approved
0.6442	Remote Similarity	NPD5222	Approved
0.6442	Remote Similarity	NPD7614	Phase 1
0.6437	Remote Similarity	NPD6108	Clinical (unspecified phase)
0.6436	Remote Similarity	NPD4096	Approved
0.6429	Remote Similarity	NPD6617	Approved
0.6429	Remote Similarity	NPD8130	Phase 1
0.6429	Remote Similarity	NPD6650	Approved
0.6429	Remote Similarity	NPD6649	Approved
0.6429	Remote Similarity	NPD6869	Approved
0.6429	Remote Similarity	NPD6847	Approved
0.6415	Remote Similarity	NPD7639	Approved
0.6415	Remote Similarity	NPD7640	Approved
0.64	Remote Similarity	NPD4518	Approved
0.6396	Remote Similarity	NPD6014	Approved
0.6396	Remote Similarity	NPD6012	Approved
0.6396	Remote Similarity	NPD6013	Approved
0.6392	Remote Similarity	NPD4788	Approved
0.6389	Remote Similarity	NPD5174	Approved
0.6389	Remote Similarity	NPD5175	Approved
0.6381	Remote Similarity	NPD5173	Approved
0.6381	Remote Similarity	NPD5959	Approved
0.6372	Remote Similarity	NPD6882	Approved
0.6372	Remote Similarity	NPD8297	Approved
0.6364	Remote Similarity	NPD6412	Phase 2
0.6355	Remote Similarity	NPD5223	Approved
0.6354	Remote Similarity	NPD4139	Approved
0.6354	Remote Similarity	NPD8028	Phase 2
0.6354	Remote Similarity	NPD4692	Approved
0.6316	Remote Similarity	NPD4195	Approved
0.6311	Remote Similarity	NPD5133	Approved
0.6306	Remote Similarity	NPD6686	Approved
0.6306	Remote Similarity	NPD6011	Approved
0.6292	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6283	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6273	Remote Similarity	NPD4768	Approved
0.6273	Remote Similarity	NPD4767	Approved
0.625	Remote Similarity	NPD5282	Discontinued
0.625	Remote Similarity	NPD7457	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD6052	Approved
0.6239	Remote Similarity	NPD4754	Approved
0.6228	Remote Similarity	NPD1609	Clinical (unspecified phase)
0.6216	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.619	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6168	Remote Similarity	NPD4225	Approved
0.6167	Remote Similarity	NPD3412	Clinical (unspecified phase)
0.6161	Remote Similarity	NPD4729	Approved
0.6161	Remote Similarity	NPD5128	Approved
0.6161	Remote Similarity	NPD4730	Approved
0.6148	Remote Similarity	NPD7507	Approved
0.6146	Remote Similarity	NPD7645	Phase 2
0.6117	Remote Similarity	NPD6698	Approved
0.6117	Remote Similarity	NPD46	Approved
0.6111	Remote Similarity	NPD6404	Discontinued
0.6106	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.61	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.61	Remote Similarity	NPD1696	Phase 3
0.6071	Remote Similarity	NPD6614	Approved
0.6068	Remote Similarity	NPD6274	Approved
0.6061	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD7154	Phase 3
0.6053	Remote Similarity	NPD5249	Phase 3
0.6053	Remote Similarity	NPD5247	Approved
0.6053	Remote Similarity	NPD5248	Approved
0.6053	Remote Similarity	NPD5250	Approved
0.6053	Remote Similarity	NPD4634	Approved
0.6053	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD5251	Approved
0.605	Remote Similarity	NPD7101	Approved
0.605	Remote Similarity	NPD7100	Approved
0.6032	Remote Similarity	NPD7260	Phase 2
0.6	Remote Similarity	NPD5215	Approved
0.6	Remote Similarity	NPD7319	Approved
0.6	Remote Similarity	NPD6059	Approved
0.6	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6	Remote Similarity	NPD5217	Approved
0.6	Remote Similarity	NPD287	Approved
0.6	Remote Similarity	NPD6054	Approved
0.6	Remote Similarity	NPD5216	Approved
0.5966	Remote Similarity	NPD6335	Approved
0.5962	Remote Similarity	NPD5785	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