NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	401.98
Volume:	307.861
LogP:	5.646
LogD:	4.215
LogS:	-5.687
# Rotatable Bonds:	0
TPSA:	29.46
# H-Bond Aceptor:	2
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	4.069
Fsp3:	0.625
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.673
MDCK Permeability:	1.7684214981272817e-05
Pgp-inhibitor:	0.774
Pgp-substrate:	0.0
Human Intestinal Absorption (HIA):	0.037
20% Bioavailability (F20%):	0.006
30% Bioavailability (F30%):	0.027

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.741
Plasma Protein Binding (PPB):	97.2774429321289%
Volume Distribution (VD):	2.402
Pgp-substrate:	4.8568572998046875%

ADMET: Metabolism

CYP1A2-inhibitor:	0.713
CYP1A2-substrate:	0.61
CYP2C19-inhibitor:	0.823
CYP2C19-substrate:	0.539
CYP2C9-inhibitor:	0.921
CYP2C9-substrate:	0.912
CYP2D6-inhibitor:	0.517
CYP2D6-substrate:	0.898
CYP3A4-inhibitor:	0.254
CYP3A4-substrate:	0.42

ADMET: Excretion

Clearance (CL):	3.35
Half-life (T1/2):	0.167

ADMET: Toxicity

hERG Blockers:	0.012
Human Hepatotoxicity (H-HT):	0.615
Drug-inuced Liver Injury (DILI):	0.242
AMES Toxicity:	0.021
Rat Oral Acute Toxicity:	0.463
Maximum Recommended Daily Dose:	0.948
Skin Sensitization:	0.432
Carcinogencity:	0.341
Eye Corrosion:	0.312
Eye Irritation:	0.927
Respiratory Toxicity:	0.961

Download Data

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

Natural Product: NPC474850

Natural Product ID:	NPC474850
*Common Name:**	Cymobarbatol
IUPAC Name:	(7S,8aS,10aR)-3,7-dibromo-8,8,10a-trimethyl-6,7,8a,9-tetrahydro-5H-xanthen-2-ol
Synonyms:	Cymobarbatol
Standard InCHIKey:	ALTFOIOEOXFNOO-OFQRWUPVSA-N
Standard InCHI:	InChI=1S/C16H20Br2O2/c1-15(2)13-7-9-6-11(19)10(17)8-12(9)20-16(13,3)5-4-14(15)18/h6,8,13-14,19H,4-5,7H2,1-3H3/t13-,14-,16+/m0/s1
SMILES:	Br[C@H]1CC[C@@]2([C@H](C1(C)C)Cc1c(O2)cc(c(c1)O)Br)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL485050
PubChem CID:	130296
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000123] Benzopyrans [CHEMONTID:0003410] 1-benzopyrans [CHEMONTID:0002817] Dibenzopyrans [CHEMONTID:0000200] Xanthenes

*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
NPO40756	Natural products	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[1479376]
NPO19445	Cymopolia barbata	Species	Dasycladaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[2691635]
NPO19445	Cymopolia barbata	Species	Dasycladaceae	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
Others	2

Activity Type	# Activity
Organism	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Inhibition	=	80.0	%	PMID[525534]
NPT566	Organism	Salmonella typhimurium	Salmonella enterica subsp. enterica serovar Typhimurium	Activity	=	80.0	%	PMID[525535]

☑ 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 NPC474850 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	2113
0.2-0.3	6313
0.3-0.4	13325
0.4-0.5	5105
0.5-0.6	12412
0.6-0.7	2727
0.7-0.8	137
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC474851
0.8248	Intermediate Similarity	NPC248557
0.8014	Intermediate Similarity	NPC47288
0.7941	Intermediate Similarity	NPC51341
0.7926	Intermediate Similarity	NPC238176
0.7926	Intermediate Similarity	NPC187993
0.7899	Intermediate Similarity	NPC168707
0.7899	Intermediate Similarity	NPC48623
0.7895	Intermediate Similarity	NPC76400
0.7857	Intermediate Similarity	NPC61685
0.7852	Intermediate Similarity	NPC69539
0.7847	Intermediate Similarity	NPC153019
0.7826	Intermediate Similarity	NPC45663
0.781	Intermediate Similarity	NPC471449
0.7793	Intermediate Similarity	NPC27578
0.7793	Intermediate Similarity	NPC289624
0.777	Intermediate Similarity	NPC475839
0.7762	Intermediate Similarity	NPC176590
0.7754	Intermediate Similarity	NPC474131
0.7746	Intermediate Similarity	NPC475361
0.774	Intermediate Similarity	NPC211352
0.7681	Intermediate Similarity	NPC32152
0.7647	Intermediate Similarity	NPC473718
0.7626	Intermediate Similarity	NPC232295
0.7609	Intermediate Similarity	NPC139047
0.7584	Intermediate Similarity	NPC474610
0.7556	Intermediate Similarity	NPC474920
0.7556	Intermediate Similarity	NPC98372
0.7517	Intermediate Similarity	NPC281499
0.7516	Intermediate Similarity	NPC38980
0.75	Intermediate Similarity	NPC128321
0.7483	Intermediate Similarity	NPC474237
0.7481	Intermediate Similarity	NPC275627
0.7465	Intermediate Similarity	NPC204535
0.7465	Intermediate Similarity	NPC46586
0.7464	Intermediate Similarity	NPC242580
0.7464	Intermediate Similarity	NPC236070
0.7464	Intermediate Similarity	NPC126759
0.7434	Intermediate Similarity	NPC79372
0.7434	Intermediate Similarity	NPC76312
0.7434	Intermediate Similarity	NPC472794
0.7434	Intermediate Similarity	NPC473049
0.7413	Intermediate Similarity	NPC474130
0.74	Intermediate Similarity	NPC327382
0.7386	Intermediate Similarity	NPC472791
0.7386	Intermediate Similarity	NPC472792
0.7386	Intermediate Similarity	NPC125861
0.7365	Intermediate Similarity	NPC158078
0.7361	Intermediate Similarity	NPC147896
0.7361	Intermediate Similarity	NPC190086
0.7361	Intermediate Similarity	NPC276962
0.7357	Intermediate Similarity	NPC283616
0.7355	Intermediate Similarity	NPC109346
0.7353	Intermediate Similarity	NPC266937
0.7353	Intermediate Similarity	NPC77772
0.7353	Intermediate Similarity	NPC470770
0.7347	Intermediate Similarity	NPC472797
0.7347	Intermediate Similarity	NPC222108
0.7347	Intermediate Similarity	NPC96719
0.7347	Intermediate Similarity	NPC206028
0.7343	Intermediate Similarity	NPC473464
0.7343	Intermediate Similarity	NPC302211
0.7343	Intermediate Similarity	NPC476332
0.7342	Intermediate Similarity	NPC7398
0.7324	Intermediate Similarity	NPC212559
0.7324	Intermediate Similarity	NPC129176
0.732	Intermediate Similarity	NPC252901
0.7315	Intermediate Similarity	NPC472798
0.7313	Intermediate Similarity	NPC320439
0.731	Intermediate Similarity	NPC133407
0.731	Intermediate Similarity	NPC252962
0.731	Intermediate Similarity	NPC28476
0.7299	Intermediate Similarity	NPC62867
0.7299	Intermediate Similarity	NPC177962
0.7297	Intermediate Similarity	NPC196193
0.7297	Intermediate Similarity	NPC196621
0.7292	Intermediate Similarity	NPC261992
0.7292	Intermediate Similarity	NPC96940
0.7273	Intermediate Similarity	NPC89341
0.7255	Intermediate Similarity	NPC265335
0.7248	Intermediate Similarity	NPC474200
0.7248	Intermediate Similarity	NPC258073
0.7248	Intermediate Similarity	NPC160623
0.7244	Intermediate Similarity	NPC474599
0.7241	Intermediate Similarity	NPC236265
0.723	Intermediate Similarity	NPC472795
0.723	Intermediate Similarity	NPC16577
0.723	Intermediate Similarity	NPC472796
0.723	Intermediate Similarity	NPC266868
0.7226	Intermediate Similarity	NPC323126
0.7222	Intermediate Similarity	NPC188997
0.7219	Intermediate Similarity	NPC312155
0.7214	Intermediate Similarity	NPC141001
0.7211	Intermediate Similarity	NPC473134
0.7203	Intermediate Similarity	NPC473875
0.72	Intermediate Similarity	NPC85595
0.7197	Intermediate Similarity	NPC472457
0.7197	Intermediate Similarity	NPC90645
0.7194	Intermediate Similarity	NPC471534
0.7185	Intermediate Similarity	NPC233320
0.7181	Intermediate Similarity	NPC475880
0.7162	Intermediate Similarity	NPC81261
0.7162	Intermediate Similarity	NPC38604
0.7162	Intermediate Similarity	NPC211179
0.7143	Intermediate Similarity	NPC160932
0.7143	Intermediate Similarity	NPC19869
0.7133	Intermediate Similarity	NPC474246
0.7133	Intermediate Similarity	NPC474143
0.7133	Intermediate Similarity	NPC43613
0.7124	Intermediate Similarity	NPC472800
0.7114	Intermediate Similarity	NPC59654
0.7114	Intermediate Similarity	NPC271832
0.7105	Intermediate Similarity	NPC27394
0.7105	Intermediate Similarity	NPC71372
0.7103	Intermediate Similarity	NPC152946
0.7095	Intermediate Similarity	NPC186889
0.7092	Intermediate Similarity	NPC290470
0.7092	Intermediate Similarity	NPC154256
0.7086	Intermediate Similarity	NPC300678
0.7083	Intermediate Similarity	NPC277798
0.7083	Intermediate Similarity	NPC100108
0.7083	Intermediate Similarity	NPC96423
0.7078	Intermediate Similarity	NPC156356
0.7075	Intermediate Similarity	NPC4286
0.7075	Intermediate Similarity	NPC124030
0.7075	Intermediate Similarity	NPC76119
0.7071	Intermediate Similarity	NPC94217
0.7067	Intermediate Similarity	NPC475102
0.7067	Intermediate Similarity	NPC249425
0.7048	Intermediate Similarity	NPC471541
0.7047	Intermediate Similarity	NPC53986
0.7047	Intermediate Similarity	NPC223912
0.7047	Intermediate Similarity	NPC38664
0.7044	Intermediate Similarity	NPC113862
0.7044	Intermediate Similarity	NPC88896
0.7034	Intermediate Similarity	NPC476165
0.7027	Intermediate Similarity	NPC50315
0.7027	Intermediate Similarity	NPC26879
0.7027	Intermediate Similarity	NPC230479
0.7027	Intermediate Similarity	NPC283049
0.7025	Intermediate Similarity	NPC316691
0.7021	Intermediate Similarity	NPC301321
0.7021	Intermediate Similarity	NPC283169
0.702	Intermediate Similarity	NPC244888
0.702	Intermediate Similarity	NPC211413
0.702	Intermediate Similarity	NPC472590
0.702	Intermediate Similarity	NPC68205
0.702	Intermediate Similarity	NPC293203
0.702	Intermediate Similarity	NPC118683
0.702	Intermediate Similarity	NPC164804
0.7019	Intermediate Similarity	NPC152947
0.7015	Intermediate Similarity	NPC269212
0.7014	Intermediate Similarity	NPC260832
0.7014	Intermediate Similarity	NPC135467
0.7013	Intermediate Similarity	NPC173660
0.7	Intermediate Similarity	NPC33244
0.7	Intermediate Similarity	NPC35344
0.7	Intermediate Similarity	NPC141003
0.7	Intermediate Similarity	NPC93962
0.6993	Remote Similarity	NPC473107
0.6987	Remote Similarity	NPC198038
0.6987	Remote Similarity	NPC259519
0.6986	Remote Similarity	NPC150026
0.6986	Remote Similarity	NPC74137
0.6985	Remote Similarity	NPC155072
0.6985	Remote Similarity	NPC53740
0.6985	Remote Similarity	NPC30416
0.6981	Remote Similarity	NPC471600
0.6981	Remote Similarity	NPC292256
0.698	Remote Similarity	NPC122359
0.698	Remote Similarity	NPC142087
0.698	Remote Similarity	NPC159987
0.698	Remote Similarity	NPC78061
0.698	Remote Similarity	NPC95034
0.698	Remote Similarity	NPC46978
0.698	Remote Similarity	NPC156298
0.6974	Remote Similarity	NPC469611
0.6974	Remote Similarity	NPC51262
0.6974	Remote Similarity	NPC13005
0.6974	Remote Similarity	NPC118253
0.6972	Remote Similarity	NPC312105
0.6968	Remote Similarity	NPC98804
0.6966	Remote Similarity	NPC475529
0.6966	Remote Similarity	NPC218753
0.6959	Remote Similarity	NPC81641
0.6957	Remote Similarity	NPC212142
0.6954	Remote Similarity	NPC325003
0.6954	Remote Similarity	NPC160081
0.6954	Remote Similarity	NPC11449
0.6954	Remote Similarity	NPC27187
0.6954	Remote Similarity	NPC226493
0.6954	Remote Similarity	NPC470225
0.695	Remote Similarity	NPC470837
0.6948	Remote Similarity	NPC195022
0.6944	Remote Similarity	NPC323074
0.6944	Remote Similarity	NPC38483
0.6943	Remote Similarity	NPC35216
0.6939	Remote Similarity	NPC474169
0.6939	Remote Similarity	NPC473572
0.6937	Remote Similarity	NPC471608

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 NPC474850 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	473
0.1-0.2	1042
0.2-0.3	1951
0.3-0.4	3023
0.4-0.5	1604
0.5-0.6	914
0.6-0.7	134
0.7-0.8	9
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
0.7778	Intermediate Similarity	NPD6671	Approved
0.7483	Intermediate Similarity	NPD6696	Suspended
0.7464	Intermediate Similarity	NPD7340	Approved
0.7372	Intermediate Similarity	NPD1398	Phase 1
0.7329	Intermediate Similarity	NPD2861	Phase 2
0.7297	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7292	Intermediate Similarity	NPD4749	Approved
0.723	Intermediate Similarity	NPD4625	Phase 3
0.7078	Intermediate Similarity	NPD6100	Approved
0.7078	Intermediate Similarity	NPD6099	Approved
0.6939	Remote Similarity	NPD3600	Clinical (unspecified phase)
0.6871	Remote Similarity	NPD2233	Approved
0.6871	Remote Similarity	NPD2232	Approved
0.6871	Remote Similarity	NPD2230	Approved
0.6866	Remote Similarity	NPD289	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD4060	Phase 1
0.6861	Remote Similarity	NPD968	Approved
0.6849	Remote Similarity	NPD3496	Discontinued
0.6842	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD5327	Phase 3
0.6821	Remote Similarity	NPD4908	Phase 1
0.6809	Remote Similarity	NPD7635	Approved
0.6806	Remote Similarity	NPD7644	Approved
0.6803	Remote Similarity	NPD1610	Phase 2
0.6803	Remote Similarity	NPD1611	Approved
0.68	Remote Similarity	NPD4624	Approved
0.68	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6774	Remote Similarity	NPD6353	Approved
0.6753	Remote Similarity	NPD4140	Approved
0.6715	Remote Similarity	NPD9244	Approved
0.671	Remote Similarity	NPD5735	Approved
0.6667	Remote Similarity	NPD2296	Approved
0.6667	Remote Similarity	NPD7095	Approved
0.6667	Remote Similarity	NPD4097	Suspended
0.6667	Remote Similarity	NPD4288	Approved
0.6667	Remote Similarity	NPD2802	Phase 3
0.6645	Remote Similarity	NPD3620	Phase 2
0.6645	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6645	Remote Similarity	NPD1530	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD2797	Approved
0.6601	Remote Similarity	NPD1529	Clinical (unspecified phase)
0.6599	Remote Similarity	NPD5585	Approved
0.6585	Remote Similarity	NPD6090	Discontinued
0.6581	Remote Similarity	NPD4870	Approved
0.6579	Remote Similarity	NPD6584	Phase 3
0.6554	Remote Similarity	NPD4626	Approved
0.6552	Remote Similarity	NPD7157	Approved
0.6533	Remote Similarity	NPD2231	Phase 2
0.6533	Remote Similarity	NPD2235	Phase 2
0.6532	Remote Similarity	NPD4010	Discontinued
0.6522	Remote Similarity	NPD5698	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD5929	Approved
0.6494	Remote Similarity	NPD6687	Approved
0.6494	Remote Similarity	NPD6688	Approved
0.6474	Remote Similarity	NPD8032	Phase 2
0.6447	Remote Similarity	NPD8651	Approved
0.6444	Remote Similarity	NPD3337	Discontinued
0.6443	Remote Similarity	NPD1778	Approved
0.6443	Remote Similarity	NPD4059	Approved
0.6438	Remote Similarity	NPD709	Approved
0.6433	Remote Similarity	NPD2238	Phase 2
0.6433	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6433	Remote Similarity	NPD1613	Approved
0.6429	Remote Similarity	NPD1712	Approved
0.6429	Remote Similarity	NPD2237	Approved
0.6424	Remote Similarity	NPD1608	Approved
0.6423	Remote Similarity	NPD3020	Approved
0.6419	Remote Similarity	NPD3091	Approved
0.6419	Remote Similarity	NPD1548	Phase 1
0.6414	Remote Similarity	NPD5283	Phase 1
0.641	Remote Similarity	NPD3268	Approved
0.641	Remote Similarity	NPD7985	Registered
0.6408	Remote Similarity	NPD2684	Approved
0.6405	Remote Similarity	NPD4098	Discontinued
0.6398	Remote Similarity	NPD5763	Approved
0.6398	Remote Similarity	NPD2346	Discontinued
0.6398	Remote Similarity	NPD5762	Approved
0.6397	Remote Similarity	NPD288	Approved
0.6382	Remote Similarity	NPD6582	Phase 2
0.6382	Remote Similarity	NPD4359	Approved
0.6382	Remote Similarity	NPD6583	Phase 3
0.6376	Remote Similarity	NPD3445	Approved
0.6376	Remote Similarity	NPD3443	Approved
0.6376	Remote Similarity	NPD5691	Approved
0.6376	Remote Similarity	NPD3444	Approved
0.6364	Remote Similarity	NPD4750	Phase 3
0.6358	Remote Similarity	NPD7037	Approved
0.6352	Remote Similarity	NPD2157	Approved
0.6345	Remote Similarity	NPD5535	Approved
0.6338	Remote Similarity	NPD2342	Discontinued
0.6338	Remote Similarity	NPD290	Approved
0.6335	Remote Similarity	NPD2935	Discontinued
0.6333	Remote Similarity	NPD2932	Approved
0.6333	Remote Similarity	NPD2668	Approved
0.6333	Remote Similarity	NPD3019	Approved
0.6333	Remote Similarity	NPD2667	Approved
0.6325	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6324	Remote Similarity	NPD1809	Phase 2
0.6324	Remote Similarity	NPD844	Approved
0.6319	Remote Similarity	NPD6674	Discontinued
0.6312	Remote Similarity	NPD7097	Phase 1
0.631	Remote Similarity	NPD2370	Clinical (unspecified phase)
0.6296	Remote Similarity	NPD845	Approved
0.6296	Remote Similarity	NPD7030	Discontinued
0.6276	Remote Similarity	NPD228	Approved
0.6265	Remote Similarity	NPD7041	Phase 2
0.6265	Remote Similarity	NPD7040	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3022	Approved
0.625	Remote Similarity	NPD1535	Discovery
0.625	Remote Similarity	NPD3021	Approved
0.625	Remote Similarity	NPD1432	Clinical (unspecified phase)
0.625	Remote Similarity	NPD3092	Approved
0.6243	Remote Similarity	NPD1298	Discontinued
0.6234	Remote Similarity	NPD1283	Approved
0.6233	Remote Similarity	NPD7843	Approved
0.6225	Remote Similarity	NPD17	Approved
0.6218	Remote Similarity	NPD5736	Approved
0.6216	Remote Similarity	NPD2557	Approved
0.6216	Remote Similarity	NPD6387	Discontinued
0.6209	Remote Similarity	NPD1481	Phase 2
0.6204	Remote Similarity	NPD2859	Approved
0.6204	Remote Similarity	NPD2860	Approved
0.6203	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6194	Remote Similarity	NPD3094	Phase 2
0.619	Remote Similarity	NPD6273	Approved
0.6188	Remote Similarity	NPD6355	Discontinued
0.6183	Remote Similarity	NPD4287	Approved
0.6182	Remote Similarity	NPD7003	Approved
0.6182	Remote Similarity	NPD7976	Clinical (unspecified phase)
0.6176	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD2799	Discontinued
0.6173	Remote Similarity	NPD6029	Clinical (unspecified phase)
0.6173	Remote Similarity	NPD4108	Discontinued
0.6173	Remote Similarity	NPD6028	Clinical (unspecified phase)
0.6169	Remote Similarity	NPD1669	Approved
0.6164	Remote Similarity	NPD7477	Discontinued
0.6159	Remote Similarity	NPD1651	Approved
0.6159	Remote Similarity	NPD6382	Discontinued
0.6154	Remote Similarity	NPD3691	Phase 2
0.6154	Remote Similarity	NPD2798	Approved
0.6154	Remote Similarity	NPD3690	Phase 2
0.6145	Remote Similarity	NPD3692	Discontinued
0.6144	Remote Similarity	NPD5351	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD5350	Clinical (unspecified phase)
0.6144	Remote Similarity	NPD422	Phase 1
0.6144	Remote Similarity	NPD1091	Approved
0.6139	Remote Similarity	NPD3027	Phase 3
0.6138	Remote Similarity	NPD1792	Phase 2
0.6138	Remote Similarity	NPD5451	Approved
0.6135	Remote Similarity	NPD4477	Approved
0.6135	Remote Similarity	NPD6032	Approved
0.6135	Remote Similarity	NPD4476	Approved
0.6131	Remote Similarity	NPD4160	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD1754	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD2933	Approved
0.6131	Remote Similarity	NPD2934	Approved
0.6131	Remote Similarity	NPD7446	Clinical (unspecified phase)
0.6125	Remote Similarity	NPD3109	Approved
0.6125	Remote Similarity	NPD3110	Approved
0.6122	Remote Similarity	NPD1138	Approved
0.6122	Remote Similarity	NPD821	Approved
0.6121	Remote Similarity	NPD5177	Phase 3
0.6118	Remote Similarity	NPD6516	Phase 2
0.6118	Remote Similarity	NPD3095	Discontinued
0.6118	Remote Similarity	NPD5846	Approved
0.6114	Remote Similarity	NPD3453	Discontinued
0.6111	Remote Similarity	NPD4538	Approved
0.6111	Remote Similarity	NPD4536	Approved
0.6111	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6104	Remote Similarity	NPD1840	Phase 2
0.6101	Remote Similarity	NPD2313	Discontinued
0.6101	Remote Similarity	NPD6798	Discontinued
0.6101	Remote Similarity	NPD7294	Phase 1
0.609	Remote Similarity	NPD3266	Approved
0.609	Remote Similarity	NPD3267	Approved
0.6089	Remote Similarity	NPD27	Approved
0.6089	Remote Similarity	NPD2489	Approved
0.6087	Remote Similarity	NPD4622	Approved
0.6087	Remote Similarity	NPD3657	Discovery
0.6087	Remote Similarity	NPD4618	Approved
0.6087	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.6087	Remote Similarity	NPD5124	Phase 1
0.6084	Remote Similarity	NPD7982	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD4110	Phase 3
0.6084	Remote Similarity	NPD4109	Clinical (unspecified phase)
0.6084	Remote Similarity	NPD3892	Phase 2
0.6084	Remote Similarity	NPD6331	Phase 2
0.6082	Remote Similarity	NPD3226	Approved
0.6076	Remote Similarity	NPD600	Approved
0.6076	Remote Similarity	NPD596	Approved
0.6074	Remote Similarity	NPD7033	Discontinued
0.6074	Remote Similarity	NPD4308	Phase 3
0.6074	Remote Similarity	NPD2155	Approved
0.6074	Remote Similarity	NPD2154	Approved
0.6074	Remote Similarity	NPD2156	Approved
0.6069	Remote Similarity	NPD5722	Discontinued
0.6062	Remote Similarity	NPD4474	Approved
0.6062	Remote Similarity	NPD4475	Approved
0.6062	Remote Similarity	NPD6663	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