NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	662.4
Volume:	665.322
LogP:	4.487
LogD:	3.855
LogS:	-4.404
# Rotatable Bonds:	4
TPSA:	144.14
# H-Bond Aceptor:	10
# H-Bond Donor:	4
# Rings:	8
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	7.387
Fsp3:	0.973
Lipinski Rule-of-5:	Accepted
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:	-5.373
MDCK Permeability:	3.820447454927489e-05
Pgp-inhibitor:	0.976
Pgp-substrate:	0.983
Human Intestinal Absorption (HIA):	0.011
20% Bioavailability (F20%):	0.003
30% Bioavailability (F30%):	0.44

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.007
Plasma Protein Binding (PPB):	83.63839721679688%
Volume Distribution (VD):	0.867
Pgp-substrate:	6.262258529663086%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.607
CYP2C19-inhibitor:	0.005
CYP2C19-substrate:	0.648
CYP2C9-inhibitor:	0.04
CYP2C9-substrate:	0.021
CYP2D6-inhibitor:	0.022
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.38
CYP3A4-substrate:	0.249

ADMET: Excretion

Clearance (CL):	1.241
Half-life (T1/2):	0.461

ADMET: Toxicity

hERG Blockers:	0.66
Human Hepatotoxicity (H-HT):	0.896
Drug-inuced Liver Injury (DILI):	0.169
AMES Toxicity:	0.013
Rat Oral Acute Toxicity:	0.255
Maximum Recommended Daily Dose:	0.892
Skin Sensitization:	0.418
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC476839

Natural Product ID:	NPC476839
*Common Name:**	Neocimicigenoside B
IUPAC Name:	[(1S,2R,3S,4R,7R,9S,12R,14S,17R,18R,19R,21R,22S)-2-hydroxy-3,8,8,17,19,23,23-heptamethyl-9-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-24,25-dioxaheptacyclo[19.3.1.01,18.03,17.04,14.07,12.012,14]pentacosan-22-yl] acetate
Synonyms:	neocimicigenoside B
Standard InCHIKey:	TWFVBWUFOFPXEY-GEOUWNACSA-N
Standard InCHI:	InChI=1S/C37H58O10/c1-18-15-21-28(44-19(2)38)32(5,6)47-37(46-21)27(18)33(7)13-14-36-17-35(36)12-11-24(45-29-26(41)25(40)20(39)16-43-29)31(3,4)22(35)9-10-23(36)34(33,8)30(37)42/h18,20-30,39-42H,9-17H2,1-8H3/t18-,20-,21-,22+,23+,24+,25+,26-,27-,28+,29+,30-,33-,34-,35-,36+,37+/m1/s1
SMILES:	C[C@@H]1C[C@@H]2[C@@H](C(O[C@]3([C@H]1[C@]4(CC[C@@]56C[C@@]57CC[C@@H](C([C@@H]7CC[C@H]6[C@@]4([C@H]3O)C)(C)C)O[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)C)O2)(C)C)OC(=O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44583840
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0002321] Cycloartanols and derivatives

*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
NPO30875	Cimicifuga racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14980692]
NPO30875	Cimicifuga racemosa	Species	Ranunculaceae	Eukaryota	rhizome	n.a.	n.a.	PMID[14980692]
NPO30875	Cimicifuga racemosa	Species	Ranunculaceae	Eukaryota	rhizomes	n.a.	n.a.	PMID[16724852]
NPO30875	Cimicifuga racemosa	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]

☑ 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
Others	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT7191	Cell Line	AtT20	Mus musculus	Activity	=	7.2	ug/ml	PMID[16724852]

☑ 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 NPC476839 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	559
0.1-0.2	4733
0.2-0.3	13192
0.3-0.4	10558
0.4-0.5	5752
0.5-0.6	3923
0.6-0.7	2290
0.7-0.8	1313
0.8-0.85	167
0.85-0.9	168
0.9-0.95	29
0.95-1	13

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476838
0.9684	High Similarity	NPC114700
0.9684	High Similarity	NPC134967
0.9684	High Similarity	NPC310138
0.9684	High Similarity	NPC470029
0.9579	High Similarity	NPC472081
0.9579	High Similarity	NPC476512
0.9579	High Similarity	NPC108227
0.9468	High Similarity	NPC210157
0.9468	High Similarity	NPC470591
0.9381	High Similarity	NPC476837
0.9381	High Similarity	NPC97260
0.9381	High Similarity	NPC139181
0.9362	High Similarity	NPC296936
0.9355	High Similarity	NPC151214
0.9355	High Similarity	NPC191915
0.9263	High Similarity	NPC470028
0.9263	High Similarity	NPC233649
0.9255	High Similarity	NPC57964
0.9255	High Similarity	NPC94582
0.9247	High Similarity	NPC473726
0.9175	High Similarity	NPC475574
0.9158	High Similarity	NPC156377
0.9158	High Similarity	NPC476510
0.9158	High Similarity	NPC203434
0.9158	High Similarity	NPC142264
0.9158	High Similarity	NPC237071
0.9158	High Similarity	NPC238796
0.9158	High Similarity	NPC252056
0.9149	High Similarity	NPC309866
0.9072	High Similarity	NPC470030
0.9053	High Similarity	NPC474399
0.9053	High Similarity	NPC473064
0.9053	High Similarity	NPC473067
0.9053	High Similarity	NPC473065
0.9053	High Similarity	NPC92196
0.9043	High Similarity	NPC137004
0.9043	High Similarity	NPC172838
0.9032	High Similarity	NPC65550
0.8958	High Similarity	NPC139271
0.8958	High Similarity	NPC304011
0.8947	High Similarity	NPC179859
0.8947	High Similarity	NPC45959
0.8947	High Similarity	NPC174024
0.8947	High Similarity	NPC291547
0.8947	High Similarity	NPC175
0.8947	High Similarity	NPC312678
0.8947	High Similarity	NPC131693
0.8947	High Similarity	NPC252253
0.8947	High Similarity	NPC253268
0.8947	High Similarity	NPC473851
0.8947	High Similarity	NPC475436
0.8936	High Similarity	NPC36372
0.8936	High Similarity	NPC473830
0.8936	High Similarity	NPC204881
0.8925	High Similarity	NPC131466
0.8925	High Similarity	NPC102725
0.8866	High Similarity	NPC475207
0.8866	High Similarity	NPC274200
0.8842	High Similarity	NPC141769
0.8842	High Similarity	NPC88962
0.8842	High Similarity	NPC250393
0.8842	High Similarity	NPC234352
0.8842	High Similarity	NPC277774
0.8842	High Similarity	NPC144790
0.8842	High Similarity	NPC48339
0.8842	High Similarity	NPC149400
0.8842	High Similarity	NPC477451
0.8842	High Similarity	NPC249204
0.8842	High Similarity	NPC325828
0.8842	High Similarity	NPC477547
0.8842	High Similarity	NPC297348
0.8842	High Similarity	NPC177834
0.883	High Similarity	NPC279329
0.883	High Similarity	NPC223143
0.8824	High Similarity	NPC472079
0.8817	High Similarity	NPC281004
0.8763	High Similarity	NPC121453
0.875	High Similarity	NPC264101
0.875	High Similarity	NPC24960
0.875	High Similarity	NPC291203
0.875	High Similarity	NPC217205
0.875	High Similarity	NPC222731
0.875	High Similarity	NPC294686
0.875	High Similarity	NPC471464
0.875	High Similarity	NPC473774
0.875	High Similarity	NPC305418
0.8737	High Similarity	NPC210759
0.8737	High Similarity	NPC473066
0.8737	High Similarity	NPC229801
0.8737	High Similarity	NPC293609
0.8737	High Similarity	NPC307167
0.8723	High Similarity	NPC473472
0.871	High Similarity	NPC140446
0.871	High Similarity	NPC43912
0.8687	High Similarity	NPC41843
0.8673	High Similarity	NPC476112
0.8673	High Similarity	NPC477223
0.8673	High Similarity	NPC307534
0.8673	High Similarity	NPC477222
0.866	High Similarity	NPC475351
0.866	High Similarity	NPC107962
0.866	High Similarity	NPC477494
0.866	High Similarity	NPC473610
0.866	High Similarity	NPC211354
0.866	High Similarity	NPC206003
0.866	High Similarity	NPC107188
0.866	High Similarity	NPC6295
0.866	High Similarity	NPC19400
0.866	High Similarity	NPC473727
0.8646	High Similarity	NPC311246
0.8646	High Similarity	NPC167644
0.8632	High Similarity	NPC473542
0.86	High Similarity	NPC477172
0.8586	High Similarity	NPC209798
0.8586	High Similarity	NPC291548
0.8586	High Similarity	NPC473518
0.8586	High Similarity	NPC471374
0.8586	High Similarity	NPC471375
0.8571	High Similarity	NPC475625
0.8571	High Similarity	NPC475643
0.8571	High Similarity	NPC470864
0.8571	High Similarity	NPC287483
0.8571	High Similarity	NPC470865
0.8571	High Similarity	NPC284104
0.8571	High Similarity	NPC473287
0.8571	High Similarity	NPC116756
0.8571	High Similarity	NPC128572
0.8571	High Similarity	NPC232037
0.8571	High Similarity	NPC84111
0.8571	High Similarity	NPC160426
0.8571	High Similarity	NPC184617
0.8571	High Similarity	NPC30856
0.8571	High Similarity	NPC98018
0.8571	High Similarity	NPC132080
0.8571	High Similarity	NPC470863
0.8571	High Similarity	NPC469824
0.8571	High Similarity	NPC470866
0.8571	High Similarity	NPC103616
0.8571	High Similarity	NPC195297
0.8571	High Similarity	NPC473601
0.8571	High Similarity	NPC97700
0.8557	High Similarity	NPC3538
0.8557	High Similarity	NPC473503
0.8557	High Similarity	NPC113500
0.8557	High Similarity	NPC30687
0.8557	High Similarity	NPC475325
0.8557	High Similarity	NPC477224
0.8542	High Similarity	NPC473637
0.8542	High Similarity	NPC5632
0.8542	High Similarity	NPC149966
0.8542	High Similarity	NPC476668
0.8542	High Similarity	NPC59006
0.8529	High Similarity	NPC469827
0.8526	High Similarity	NPC228059
0.8526	High Similarity	NPC82955
0.8515	High Similarity	NPC80191
0.8515	High Similarity	NPC310031
0.85	High Similarity	NPC471426
0.85	High Similarity	NPC471427
0.85	High Similarity	NPC51579
0.85	High Similarity	NPC471428
0.85	High Similarity	NPC20028
0.8495	Intermediate Similarity	NPC290612
0.8491	Intermediate Similarity	NPC477489
0.8485	Intermediate Similarity	NPC470861
0.8485	Intermediate Similarity	NPC470862
0.8485	Intermediate Similarity	NPC303069
0.8485	Intermediate Similarity	NPC83137
0.8485	Intermediate Similarity	NPC51520
0.8485	Intermediate Similarity	NPC232611
0.8485	Intermediate Similarity	NPC115165
0.8469	Intermediate Similarity	NPC469710
0.8469	Intermediate Similarity	NPC215570
0.8462	Intermediate Similarity	NPC469826
0.8454	Intermediate Similarity	NPC476669
0.84	Intermediate Similarity	NPC292775
0.84	Intermediate Similarity	NPC473616
0.8387	Intermediate Similarity	NPC474156
0.8381	Intermediate Similarity	NPC227879
0.8381	Intermediate Similarity	NPC236753
0.8381	Intermediate Similarity	NPC208333
0.8381	Intermediate Similarity	NPC228190
0.8365	Intermediate Similarity	NPC203974
0.8333	Intermediate Similarity	NPC20822
0.8318	Intermediate Similarity	NPC477492
0.83	Intermediate Similarity	NPC472273
0.8286	Intermediate Similarity	NPC472988
0.8286	Intermediate Similarity	NPC38217
0.8283	Intermediate Similarity	NPC21897
0.8269	Intermediate Similarity	NPC215408
0.8269	Intermediate Similarity	NPC165405
0.8265	Intermediate Similarity	NPC224003
0.8265	Intermediate Similarity	NPC171741
0.8265	Intermediate Similarity	NPC211845
0.8265	Intermediate Similarity	NPC256104
0.8265	Intermediate Similarity	NPC323231
0.8265	Intermediate Similarity	NPC182740
0.8265	Intermediate Similarity	NPC470623
0.8265	Intermediate Similarity	NPC18724

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 NPC476839 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	574
0.1-0.2	4403
0.2-0.3	2911
0.3-0.4	663
0.4-0.5	348
0.5-0.6	198
0.6-0.7	37
0.7-0.8	14
0.8-0.85	1
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8842	High Similarity	NPD8171	Discontinued
0.835	Intermediate Similarity	NPD8170	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD8294	Approved
0.7965	Intermediate Similarity	NPD8377	Approved
0.7909	Intermediate Similarity	NPD8133	Approved
0.7895	Intermediate Similarity	NPD8380	Approved
0.7895	Intermediate Similarity	NPD8379	Approved
0.7895	Intermediate Similarity	NPD8378	Approved
0.7895	Intermediate Similarity	NPD8296	Approved
0.7895	Intermediate Similarity	NPD8335	Approved
0.7739	Intermediate Similarity	NPD8033	Approved
0.7579	Intermediate Similarity	NPD6928	Phase 2
0.7478	Intermediate Similarity	NPD7328	Approved
0.7478	Intermediate Similarity	NPD7327	Approved
0.7414	Intermediate Similarity	NPD7516	Approved
0.7143	Intermediate Similarity	NPD7503	Approved
0.708	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7049	Intermediate Similarity	NPD7507	Approved
0.7	Intermediate Similarity	NPD3670	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD3669	Approved
0.6949	Remote Similarity	NPD8295	Clinical (unspecified phase)
0.6882	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.688	Remote Similarity	NPD7319	Approved
0.6864	Remote Similarity	NPD6940	Discontinued
0.6837	Remote Similarity	NPD6697	Approved
0.6837	Remote Similarity	NPD6118	Approved
0.6837	Remote Similarity	NPD6114	Approved
0.6837	Remote Similarity	NPD6115	Approved
0.68	Remote Similarity	NPD7736	Approved
0.6771	Remote Similarity	NPD1810	Approved
0.6771	Remote Similarity	NPD1811	Approved
0.6759	Remote Similarity	NPD7991	Discontinued
0.6754	Remote Similarity	NPD6412	Phase 2
0.6735	Remote Similarity	NPD6116	Phase 1
0.6633	Remote Similarity	NPD6117	Approved
0.6613	Remote Similarity	NPD8328	Phase 3
0.6587	Remote Similarity	NPD8293	Discontinued
0.6458	Remote Similarity	NPD7532	Clinical (unspecified phase)
0.6458	Remote Similarity	NPD2687	Approved
0.6458	Remote Similarity	NPD2254	Approved
0.6458	Remote Similarity	NPD2686	Approved
0.6429	Remote Similarity	NPD6113	Clinical (unspecified phase)
0.64	Remote Similarity	NPD6370	Approved
0.6364	Remote Similarity	NPD3702	Approved
0.633	Remote Similarity	NPD8035	Phase 2
0.633	Remote Similarity	NPD8034	Phase 2
0.6311	Remote Similarity	NPD1779	Approved
0.6311	Remote Similarity	NPD1780	Approved
0.6299	Remote Similarity	NPD7492	Approved
0.6289	Remote Similarity	NPD4787	Phase 1
0.6271	Remote Similarity	NPD6686	Approved
0.6271	Remote Similarity	NPD8174	Phase 2
0.625	Remote Similarity	NPD6616	Approved
0.624	Remote Similarity	NPD6054	Approved
0.624	Remote Similarity	NPD6059	Approved
0.624	Remote Similarity	NPD6319	Approved
0.6214	Remote Similarity	NPD7625	Phase 1
0.6212	Remote Similarity	NPD8449	Approved
0.6202	Remote Similarity	NPD7078	Approved
0.6198	Remote Similarity	NPD6882	Approved
0.6198	Remote Similarity	NPD8297	Approved
0.6174	Remote Similarity	NPD1700	Approved
0.6165	Remote Similarity	NPD8450	Suspended
0.6154	Remote Similarity	NPD4056	Clinical (unspecified phase)
0.6154	Remote Similarity	NPD4057	Clinical (unspecified phase)
0.614	Remote Similarity	NPD7638	Approved
0.6129	Remote Similarity	NPD6009	Approved
0.6087	Remote Similarity	NPD7640	Approved
0.6087	Remote Similarity	NPD7639	Approved
0.6075	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.6063	Remote Similarity	NPD8513	Phase 3
0.6063	Remote Similarity	NPD6016	Approved
0.6063	Remote Similarity	NPD6015	Approved
0.6063	Remote Similarity	NPD8517	Approved
0.6063	Remote Similarity	NPD8515	Approved
0.6063	Remote Similarity	NPD8516	Approved
0.6061	Remote Similarity	NPD4809	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD4808	Clinical (unspecified phase)
0.6061	Remote Similarity	NPD5777	Approved
0.604	Remote Similarity	NPD3703	Phase 2
0.6016	Remote Similarity	NPD5988	Approved
0.6016	Remote Similarity	NPD4632	Approved
0.6	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6	Remote Similarity	NPD371	Approved
0.5983	Remote Similarity	NPD7632	Discontinued
0.5969	Remote Similarity	NPD7604	Phase 2
0.5969	Remote Similarity	NPD6067	Discontinued
0.5966	Remote Similarity	NPD6402	Approved
0.5966	Remote Similarity	NPD7128	Approved
0.5966	Remote Similarity	NPD6675	Approved
0.5966	Remote Similarity	NPD5739	Approved
0.596	Remote Similarity	NPD4245	Approved
0.596	Remote Similarity	NPD4244	Approved
0.595	Remote Similarity	NPD6373	Approved
0.595	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.595	Remote Similarity	NPD6372	Approved
0.5917	Remote Similarity	NPD7646	Clinical (unspecified phase)
0.5905	Remote Similarity	NPD7525	Registered
0.5868	Remote Similarity	NPD6899	Approved
0.5868	Remote Similarity	NPD7320	Approved
0.5868	Remote Similarity	NPD6881	Approved
0.5859	Remote Similarity	NPD3699	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3700	Clinical (unspecified phase)
0.5859	Remote Similarity	NPD3698	Phase 2
0.5854	Remote Similarity	NPD6649	Approved
0.5854	Remote Similarity	NPD8130	Phase 1
0.5854	Remote Similarity	NPD6650	Approved
0.5812	Remote Similarity	NPD8418	Phase 2
0.5789	Remote Similarity	NPD6033	Approved
0.5785	Remote Similarity	NPD5701	Approved
0.5785	Remote Similarity	NPD5697	Approved
0.5772	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.5772	Remote Similarity	NPD7102	Approved
0.5772	Remote Similarity	NPD7290	Approved
0.5772	Remote Similarity	NPD6883	Approved
0.5758	Remote Similarity	NPD5361	Clinical (unspecified phase)
0.5758	Remote Similarity	NPD5360	Phase 3
0.5748	Remote Similarity	NPD7115	Discovery
0.5743	Remote Similarity	NPD6081	Approved
0.5726	Remote Similarity	NPD8413	Clinical (unspecified phase)
0.5726	Remote Similarity	NPD6617	Approved
0.5726	Remote Similarity	NPD6869	Approved
0.5726	Remote Similarity	NPD6847	Approved
0.5714	Remote Similarity	NPD8139	Approved
0.5714	Remote Similarity	NPD8086	Approved
0.5714	Remote Similarity	NPD8082	Approved
0.5714	Remote Similarity	NPD8085	Approved
0.5714	Remote Similarity	NPD8138	Approved
0.5714	Remote Similarity	NPD8084	Approved
0.5714	Remote Similarity	NPD8083	Approved
0.5702	Remote Similarity	NPD6008	Approved
0.5692	Remote Similarity	NPD5983	Phase 2
0.5691	Remote Similarity	NPD6012	Approved
0.5691	Remote Similarity	NPD6013	Approved
0.5691	Remote Similarity	NPD6014	Approved
0.5684	Remote Similarity	NPD6123	Approved
0.5667	Remote Similarity	NPD8276	Approved
0.5667	Remote Similarity	NPD7986	Approved
0.5667	Remote Similarity	NPD7912	Approved
0.5667	Remote Similarity	NPD7987	Approved
0.5667	Remote Similarity	NPD8275	Approved
0.5667	Remote Similarity	NPD7911	Approved
0.5652	Remote Similarity	NPD7748	Approved
0.5645	Remote Similarity	NPD4634	Approved
0.5644	Remote Similarity	NPD4789	Approved
0.5641	Remote Similarity	NPD6083	Phase 2
0.5641	Remote Similarity	NPD6084	Phase 2
0.5641	Remote Similarity	NPD7902	Approved
0.5639	Remote Similarity	NPD6336	Discontinued
0.562	Remote Similarity	NPD8081	Approved
0.561	Remote Similarity	NPD6011	Approved
0.56	Remote Similarity	NPD6401	Clinical (unspecified phase)

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