NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	504.16
Volume:	470.491
LogP:	1.325
LogD:	0.639
LogS:	-3.873
# Rotatable Bonds:	4
TPSA:	161.96
# H-Bond Aceptor:	11
# H-Bond Donor:	3
# Rings:	6
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.378
Synthetic Accessibility Score:	6.686
Fsp3:	0.64
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
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:	-5.559
MDCK Permeability:	5.4331670980900526e-05
Pgp-inhibitor:	0.103
Pgp-substrate:	0.999
Human Intestinal Absorption (HIA):	0.743
20% Bioavailability (F20%):	0.896
30% Bioavailability (F30%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.161
Plasma Protein Binding (PPB):	61.84177017211914%
Volume Distribution (VD):	0.518
Pgp-substrate:	36.13330078125%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.7
CYP2C19-inhibitor:	0.013
CYP2C19-substrate:	0.073
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.029
CYP2D6-inhibitor:	0.016
CYP2D6-substrate:	0.138
CYP3A4-inhibitor:	0.188
CYP3A4-substrate:	0.191

ADMET: Excretion

Clearance (CL):	3.841
Half-life (T1/2):	0.753

ADMET: Toxicity

hERG Blockers:	0.164
Human Hepatotoxicity (H-HT):	0.904
Drug-inuced Liver Injury (DILI):	0.955
AMES Toxicity:	0.04
Rat Oral Acute Toxicity:	0.701
Maximum Recommended Daily Dose:	0.944
Skin Sensitization:	0.425
Carcinogencity:	0.242
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.938

Download Data

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

Natural Product: NPC477745

Natural Product ID:	NPC477745
*Common Name:**	Neosergeolide
IUPAC Name:	methyl (1S,2R,3R,4S,5R,8R,9S,10R,13R,15S,16S)-10-acetyloxy-3,4-dihydroxy-1,16-dimethyl-11,20-dioxo-6,12,19-trioxahexacyclo[13.7.0.02,8.05,9.08,13.018,22]docosa-17,21-diene-5-carboxylate
Synonyms:	Neosergeolide
Standard InCHIKey:	NEDSAORRUXXBSA-YLGGRGQVSA-N
Standard InCHI:	InChI=1S/C25H28O11/c1-9-5-13-12(7-15(27)35-13)23(3)11(9)6-14-24-8-33-25(22(31)32-4,20(29)16(28)18(23)24)19(24)17(21(30)36-14)34-10(2)26/h5,7,9,11,14,16-20,28-29H,6,8H2,1-4H3/t9-,11+,14-,16-,17-,18-,19-,20+,23-,24-,25-/m1/s1
SMILES:	C[C@@H]1C=C2C(=CC(=O)O2)[C@]3([C@H]1C[C@@H]4[C@]56[C@@H]3[C@H]([C@@H]([C@@]([C@@H]5[C@H](C(=O)O4)OC(=O)C)(OC6)C(=O)OC)O)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49798949
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001283] Terpene lactones [CHEMONTID:0002119] Quassinoids

*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
NPO33554	Picrolemma sprucei	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]

☑ 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
NPT485	Organism	Plasmodium falciparum (isolate K1 / Thailand)	Plasmodium falciparum K1	IC50	=	2	nM	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 NPC477745 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	280
0.1-0.2	1471
0.2-0.3	4109
0.3-0.4	6802
0.4-0.5	11054
0.5-0.6	10096
0.6-0.7	6250
0.7-0.8	2366
0.8-0.85	181
0.85-0.9	64
0.9-0.95	22
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9914	High Similarity	NPC476008
0.9402	High Similarity	NPC312833
0.9322	High Similarity	NPC105926
0.9322	High Similarity	NPC91693
0.9322	High Similarity	NPC18945
0.9322	High Similarity	NPC265557
0.9244	High Similarity	NPC476729
0.9244	High Similarity	NPC24651
0.916	High Similarity	NPC67251
0.8992	High Similarity	NPC470779
0.8983	High Similarity	NPC470777
0.8966	High Similarity	NPC143268
0.8966	High Similarity	NPC268238
0.8966	High Similarity	NPC45218
0.8966	High Similarity	NPC323821
0.8898	High Similarity	NPC17772
0.8898	High Similarity	NPC470776
0.8889	High Similarity	NPC16081
0.8889	High Similarity	NPC173686
0.8814	High Similarity	NPC473590
0.874	High Similarity	NPC262813
0.8729	High Similarity	NPC89929
0.8718	High Similarity	NPC94509
0.8718	High Similarity	NPC478212
0.8672	High Similarity	NPC251998
0.8672	High Similarity	NPC471089
0.8672	High Similarity	NPC141215
0.8672	High Similarity	NPC190065
0.8655	High Similarity	NPC470775
0.8655	High Similarity	NPC474654
0.8655	High Similarity	NPC176513
0.8655	High Similarity	NPC470778
0.8655	High Similarity	NPC97908
0.8655	High Similarity	NPC122033
0.8655	High Similarity	NPC470854
0.8655	High Similarity	NPC146432
0.8655	High Similarity	NPC287343
0.8655	High Similarity	NPC478204
0.8644	High Similarity	NPC299849
0.8618	High Similarity	NPC470922
0.8605	High Similarity	NPC596
0.8605	High Similarity	NPC140045
0.8605	High Similarity	NPC295885
0.8595	High Similarity	NPC478051
0.8583	High Similarity	NPC108581
0.8583	High Similarity	NPC478206
0.8583	High Similarity	NPC478205
0.8583	High Similarity	NPC168879
0.8583	High Similarity	NPC251310
0.8571	High Similarity	NPC40632
0.8571	High Similarity	NPC251236
0.8571	High Similarity	NPC474734
0.8571	High Similarity	NPC96312
0.8571	High Similarity	NPC190185
0.8571	High Similarity	NPC213084
0.8571	High Similarity	NPC328374
0.8559	High Similarity	NPC49451
0.8548	High Similarity	NPC181999
0.8527	High Similarity	NPC243014
0.85	High Similarity	NPC53396
0.85	High Similarity	NPC98249
0.8487	Intermediate Similarity	NPC473798
0.8462	Intermediate Similarity	NPC478209
0.8443	Intermediate Similarity	NPC107338
0.8443	Intermediate Similarity	NPC112038
0.8443	Intermediate Similarity	NPC472004
0.8443	Intermediate Similarity	NPC109607
0.843	Intermediate Similarity	NPC204552
0.843	Intermediate Similarity	NPC188667
0.843	Intermediate Similarity	NPC284707
0.843	Intermediate Similarity	NPC297179
0.8417	Intermediate Similarity	NPC478216
0.8417	Intermediate Similarity	NPC207217
0.8413	Intermediate Similarity	NPC295220
0.8413	Intermediate Similarity	NPC475636
0.8403	Intermediate Similarity	NPC208998
0.8403	Intermediate Similarity	NPC198539
0.8403	Intermediate Similarity	NPC7921
0.84	Intermediate Similarity	NPC87662
0.839	Intermediate Similarity	NPC97939
0.839	Intermediate Similarity	NPC100329
0.839	Intermediate Similarity	NPC247031
0.839	Intermediate Similarity	NPC132790
0.8376	Intermediate Similarity	NPC478210
0.8374	Intermediate Similarity	NPC477046
0.8374	Intermediate Similarity	NPC102822
0.8361	Intermediate Similarity	NPC475775
0.8361	Intermediate Similarity	NPC476529
0.8359	Intermediate Similarity	NPC102316
0.8347	Intermediate Similarity	NPC58662
0.8346	Intermediate Similarity	NPC54614
0.8346	Intermediate Similarity	NPC309096
0.8346	Intermediate Similarity	NPC476851
0.8333	Intermediate Similarity	NPC470780
0.8319	Intermediate Similarity	NPC269530
0.8305	Intermediate Similarity	NPC478211
0.8281	Intermediate Similarity	NPC476852
0.8279	Intermediate Similarity	NPC240509
0.8264	Intermediate Similarity	NPC474046
0.8264	Intermediate Similarity	NPC259306
0.8264	Intermediate Similarity	NPC470628
0.8264	Intermediate Similarity	NPC152199
0.8264	Intermediate Similarity	NPC235539
0.8264	Intermediate Similarity	NPC134869
0.825	Intermediate Similarity	NPC475966
0.824	Intermediate Similarity	NPC227397
0.8235	Intermediate Similarity	NPC469656
0.8235	Intermediate Similarity	NPC469655
0.8235	Intermediate Similarity	NPC474846
0.8235	Intermediate Similarity	NPC171888
0.8235	Intermediate Similarity	NPC146945
0.8231	Intermediate Similarity	NPC242486
0.8231	Intermediate Similarity	NPC15215
0.8226	Intermediate Similarity	NPC471999
0.8226	Intermediate Similarity	NPC472000
0.822	Intermediate Similarity	NPC27814
0.8217	Intermediate Similarity	NPC478154
0.8211	Intermediate Similarity	NPC469488
0.8205	Intermediate Similarity	NPC202524
0.8205	Intermediate Similarity	NPC302788
0.8203	Intermediate Similarity	NPC231529
0.8197	Intermediate Similarity	NPC473968
0.8197	Intermediate Similarity	NPC469684
0.8182	Intermediate Similarity	NPC474906
0.8182	Intermediate Similarity	NPC117712
0.8182	Intermediate Similarity	NPC470919
0.8182	Intermediate Similarity	NPC18547
0.8182	Intermediate Similarity	NPC178289
0.8182	Intermediate Similarity	NPC469877
0.8167	Intermediate Similarity	NPC289312
0.8167	Intermediate Similarity	NPC302146
0.8167	Intermediate Similarity	NPC474516
0.8167	Intermediate Similarity	NPC11252
0.8167	Intermediate Similarity	NPC472002
0.8154	Intermediate Similarity	NPC478151
0.8151	Intermediate Similarity	NPC472666
0.814	Intermediate Similarity	NPC476074
0.814	Intermediate Similarity	NPC478065
0.814	Intermediate Similarity	NPC475377
0.814	Intermediate Similarity	NPC172374
0.814	Intermediate Similarity	NPC475167
0.814	Intermediate Similarity	NPC45346
0.814	Intermediate Similarity	NPC25998
0.814	Intermediate Similarity	NPC262796
0.814	Intermediate Similarity	NPC134914
0.814	Intermediate Similarity	NPC173435
0.814	Intermediate Similarity	NPC478064
0.814	Intermediate Similarity	NPC264566
0.814	Intermediate Similarity	NPC478155
0.814	Intermediate Similarity	NPC329993
0.814	Intermediate Similarity	NPC301639
0.8136	Intermediate Similarity	NPC293850
0.8136	Intermediate Similarity	NPC50124
0.813	Intermediate Similarity	NPC21326
0.813	Intermediate Similarity	NPC106644
0.8125	Intermediate Similarity	NPC476859
0.8125	Intermediate Similarity	NPC188291
0.812	Intermediate Similarity	NPC34768
0.812	Intermediate Similarity	NPC478208
0.8115	Intermediate Similarity	NPC477509
0.8099	Intermediate Similarity	NPC471204
0.8099	Intermediate Similarity	NPC469496
0.8099	Intermediate Similarity	NPC33360
0.8099	Intermediate Similarity	NPC469454
0.8099	Intermediate Similarity	NPC477126
0.8099	Intermediate Similarity	NPC51978
0.8099	Intermediate Similarity	NPC469463
0.8095	Intermediate Similarity	NPC120724
0.8083	Intermediate Similarity	NPC201992
0.8083	Intermediate Similarity	NPC304180
0.8083	Intermediate Similarity	NPC179798
0.808	Intermediate Similarity	NPC275675
0.8077	Intermediate Similarity	NPC478152
0.8077	Intermediate Similarity	NPC476193
0.8077	Intermediate Similarity	NPC100390
0.8077	Intermediate Similarity	NPC478153
0.8077	Intermediate Similarity	NPC254614
0.8077	Intermediate Similarity	NPC478150
0.8065	Intermediate Similarity	NPC77689
0.8065	Intermediate Similarity	NPC9674
0.8065	Intermediate Similarity	NPC230513
0.8065	Intermediate Similarity	NPC476107
0.8065	Intermediate Similarity	NPC19028
0.8065	Intermediate Similarity	NPC268958
0.8065	Intermediate Similarity	NPC473636
0.8062	Intermediate Similarity	NPC477196
0.8062	Intermediate Similarity	NPC264192
0.8062	Intermediate Similarity	NPC476854
0.8051	Intermediate Similarity	NPC144854
0.8051	Intermediate Similarity	NPC3316
0.8049	Intermediate Similarity	NPC134430
0.8049	Intermediate Similarity	NPC13713
0.8049	Intermediate Similarity	NPC27999
0.8049	Intermediate Similarity	NPC477116
0.8047	Intermediate Similarity	NPC469757
0.8047	Intermediate Similarity	NPC146456
0.8047	Intermediate Similarity	NPC470882
0.8047	Intermediate Similarity	NPC471357
0.8047	Intermediate Similarity	NPC117702
0.8017	Intermediate Similarity	NPC42658

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 NPC477745 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	235
0.1-0.2	1582
0.2-0.3	3634
0.3-0.4	2339
0.4-0.5	777
0.5-0.6	347
0.6-0.7	161
0.7-0.8	74
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7983	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7923	Intermediate Similarity	NPD7319	Approved
0.7917	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7851	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7717	Intermediate Similarity	NPD6319	Approved
0.7692	Intermediate Similarity	NPD7507	Approved
0.7674	Intermediate Similarity	NPD8328	Phase 3
0.7603	Intermediate Similarity	NPD5954	Clinical (unspecified phase)
0.7481	Intermediate Similarity	NPD7492	Approved
0.748	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7444	Intermediate Similarity	NPD7736	Approved
0.7442	Intermediate Similarity	NPD6059	Approved
0.7442	Intermediate Similarity	NPD6054	Approved
0.7424	Intermediate Similarity	NPD6616	Approved
0.7398	Intermediate Similarity	NPD6686	Approved
0.7385	Intermediate Similarity	NPD6016	Approved
0.7385	Intermediate Similarity	NPD8517	Approved
0.7385	Intermediate Similarity	NPD8513	Phase 3
0.7385	Intermediate Similarity	NPD8515	Approved
0.7385	Intermediate Similarity	NPD6015	Approved
0.7385	Intermediate Similarity	NPD6921	Approved
0.7385	Intermediate Similarity	NPD8516	Approved
0.7368	Intermediate Similarity	NPD7078	Approved
0.7368	Intermediate Similarity	NPD8293	Discontinued
0.7364	Intermediate Similarity	NPD7516	Approved
0.7344	Intermediate Similarity	NPD7115	Discovery
0.7339	Intermediate Similarity	NPD6373	Approved
0.7339	Intermediate Similarity	NPD6372	Approved
0.7328	Intermediate Similarity	NPD6370	Approved
0.7328	Intermediate Similarity	NPD5988	Approved
0.7311	Intermediate Similarity	NPD4225	Approved
0.7302	Intermediate Similarity	NPD8297	Approved
0.7287	Intermediate Similarity	NPD7328	Approved
0.7287	Intermediate Similarity	NPD7327	Approved
0.7258	Intermediate Similarity	NPD7320	Approved
0.7252	Intermediate Similarity	NPD7503	Approved
0.7244	Intermediate Similarity	NPD4632	Approved
0.7236	Intermediate Similarity	NPD5739	Approved
0.7236	Intermediate Similarity	NPD6402	Approved
0.7236	Intermediate Similarity	NPD6675	Approved
0.7236	Intermediate Similarity	NPD7128	Approved
0.7222	Intermediate Similarity	NPD6649	Approved
0.7222	Intermediate Similarity	NPD6650	Approved
0.7177	Intermediate Similarity	NPD5697	Approved
0.7177	Intermediate Similarity	NPD5701	Approved
0.7121	Intermediate Similarity	NPD8378	Approved
0.7121	Intermediate Similarity	NPD8296	Approved
0.7121	Intermediate Similarity	NPD8380	Approved
0.7121	Intermediate Similarity	NPD8335	Approved
0.7121	Intermediate Similarity	NPD8379	Approved
0.712	Intermediate Similarity	NPD6899	Approved
0.712	Intermediate Similarity	NPD6881	Approved
0.7101	Intermediate Similarity	NPD6845	Suspended
0.7077	Intermediate Similarity	NPD6009	Approved
0.7063	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7063	Intermediate Similarity	NPD6012	Approved
0.7063	Intermediate Similarity	NPD6014	Approved
0.7063	Intermediate Similarity	NPD6013	Approved
0.7045	Intermediate Similarity	NPD8294	Approved
0.7045	Intermediate Similarity	NPD8377	Approved
0.7031	Intermediate Similarity	NPD6882	Approved
0.7029	Intermediate Similarity	NPD7260	Phase 2
0.7025	Intermediate Similarity	NPD7638	Approved
0.7008	Intermediate Similarity	NPD4634	Approved
0.7008	Intermediate Similarity	NPD7102	Approved
0.7008	Intermediate Similarity	NPD6883	Approved
0.7008	Intermediate Similarity	NPD7290	Approved
0.6992	Remote Similarity	NPD8033	Approved
0.6992	Remote Similarity	NPD5983	Phase 2
0.6985	Remote Similarity	NPD8074	Phase 3
0.6984	Remote Similarity	NPD6011	Approved
0.6967	Remote Similarity	NPD7640	Approved
0.6967	Remote Similarity	NPD7639	Approved
0.696	Remote Similarity	NPD6008	Approved
0.6953	Remote Similarity	NPD6869	Approved
0.6953	Remote Similarity	NPD8130	Phase 1
0.6953	Remote Similarity	NPD6617	Approved
0.6953	Remote Similarity	NPD6847	Approved
0.6934	Remote Similarity	NPD6033	Approved
0.6905	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD6053	Discontinued
0.6889	Remote Similarity	NPD7604	Phase 2
0.6833	Remote Similarity	NPD5282	Discontinued
0.6822	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6803	Remote Similarity	NPD4755	Approved
0.6788	Remote Similarity	NPD6336	Discontinued
0.6783	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6772	Remote Similarity	NPD6412	Phase 2
0.6748	Remote Similarity	NPD5696	Approved
0.6742	Remote Similarity	NPD6274	Approved
0.672	Remote Similarity	NPD5211	Phase 2
0.6718	Remote Similarity	NPD8133	Approved
0.6694	Remote Similarity	NPD5285	Approved
0.6694	Remote Similarity	NPD5286	Approved
0.6694	Remote Similarity	NPD4700	Approved
0.6694	Remote Similarity	NPD4696	Approved
0.6692	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6083	Phase 2
0.6667	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD6411	Approved
0.6667	Remote Similarity	NPD7902	Approved
0.6618	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6614	Remote Similarity	NPD5141	Approved
0.6612	Remote Similarity	NPD5778	Approved
0.6612	Remote Similarity	NPD5779	Approved
0.6593	Remote Similarity	NPD7101	Approved
0.6593	Remote Similarity	NPD7100	Approved
0.6587	Remote Similarity	NPD7632	Discontinued
0.6587	Remote Similarity	NPD5224	Approved
0.6587	Remote Similarity	NPD5225	Approved
0.6587	Remote Similarity	NPD5226	Approved
0.6587	Remote Similarity	NPD4633	Approved
0.6585	Remote Similarity	NPD4697	Phase 3
0.6583	Remote Similarity	NPD46	Approved
0.6583	Remote Similarity	NPD6698	Approved
0.6567	Remote Similarity	NPD6317	Approved
0.6562	Remote Similarity	NPD4768	Approved
0.6562	Remote Similarity	NPD4767	Approved
0.6557	Remote Similarity	NPD7748	Approved
0.6535	Remote Similarity	NPD5175	Approved
0.6535	Remote Similarity	NPD5174	Approved
0.6529	Remote Similarity	NPD7515	Phase 2
0.6529	Remote Similarity	NPD7983	Approved
0.6519	Remote Similarity	NPD6313	Approved
0.6519	Remote Similarity	NPD6314	Approved
0.6519	Remote Similarity	NPD6335	Approved
0.6508	Remote Similarity	NPD5344	Discontinued
0.6508	Remote Similarity	NPD1700	Approved
0.6508	Remote Similarity	NPD5223	Approved
0.6504	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6504	Remote Similarity	NPD5695	Phase 3
0.65	Remote Similarity	NPD6101	Approved
0.65	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6496	Remote Similarity	NPD6908	Approved
0.6496	Remote Similarity	NPD6909	Approved
0.6489	Remote Similarity	NPD6371	Approved
0.6471	Remote Similarity	NPD3573	Approved
0.6462	Remote Similarity	NPD4729	Approved
0.6462	Remote Similarity	NPD4730	Approved
0.6452	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD5221	Approved
0.6452	Remote Similarity	NPD5222	Approved
0.6441	Remote Similarity	NPD1694	Approved
0.6433	Remote Similarity	NPD8434	Phase 2
0.6429	Remote Similarity	NPD6648	Approved
0.6423	Remote Similarity	NPD7900	Approved
0.6423	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6406	Remote Similarity	NPD4754	Approved
0.64	Remote Similarity	NPD5173	Approved
0.6395	Remote Similarity	NPD6333	Approved
0.6395	Remote Similarity	NPD6334	Approved
0.6393	Remote Similarity	NPD5693	Phase 1
0.6387	Remote Similarity	NPD3618	Phase 1
0.6386	Remote Similarity	NPD7799	Discontinued
0.637	Remote Similarity	NPD6868	Approved
0.6364	Remote Similarity	NPD5247	Approved
0.6364	Remote Similarity	NPD5956	Approved
0.6364	Remote Similarity	NPD5249	Phase 3
0.6364	Remote Similarity	NPD5251	Approved
0.6364	Remote Similarity	NPD7285	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD5248	Approved
0.6364	Remote Similarity	NPD5328	Approved
0.6364	Remote Similarity	NPD5250	Approved
0.6341	Remote Similarity	NPD6399	Phase 3
0.6336	Remote Similarity	NPD5128	Approved
0.6325	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6316	Remote Similarity	NPD8407	Phase 2
0.6281	Remote Similarity	NPD6672	Approved
0.6281	Remote Similarity	NPD5737	Approved
0.626	Remote Similarity	NPD7637	Suspended
0.626	Remote Similarity	NPD6079	Approved
0.6258	Remote Similarity	NPD5537	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.624	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.624	Remote Similarity	NPD5210	Approved
0.624	Remote Similarity	NPD4629	Approved
0.6235	Remote Similarity	NPD8368	Discontinued
0.623	Remote Similarity	NPD4753	Phase 2
0.622	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6214	Remote Similarity	NPD8080	Discontinued
0.621	Remote Similarity	NPD4202	Approved
0.6194	Remote Similarity	NPD5217	Approved
0.6194	Remote Similarity	NPD5216	Approved
0.6194	Remote Similarity	NPD5215	Approved
0.6194	Remote Similarity	NPD7236	Approved
0.6179	Remote Similarity	NPD5692	Phase 3
0.6179	Remote Similarity	NPD7838	Discovery
0.617	Remote Similarity	NPD6067	Discontinued
0.6149	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6134	Remote Similarity	NPD6110	Phase 1
0.6129	Remote Similarity	NPD8035	Phase 2
0.6129	Remote Similarity	NPD5694	Approved
0.6129	Remote Similarity	NPD5284	Approved
0.6129	Remote Similarity	NPD5281	Approved
0.6129	Remote Similarity	NPD6050	Approved
0.6129	Remote Similarity	NPD8034	Phase 2
0.6119	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6119	Remote Similarity	NPD5169	Approved
0.6119	Remote Similarity	NPD5135	Approved
0.6116	Remote Similarity	NPD5279	Phase 3

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