NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	336.23
Volume:	358.695
LogP:	1.452
LogD:	1.508
LogS:	-2.247
# Rotatable Bonds:	3
TPSA:	74.6
# H-Bond Aceptor:	4
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.614
Synthetic Accessibility Score:	4.787
Fsp3:	0.9
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	1
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.869
MDCK Permeability:	7.263731731654843e-06
Pgp-inhibitor:	0.714
Pgp-substrate:	0.276
Human Intestinal Absorption (HIA):	0.009
20% Bioavailability (F20%):	0.01
30% Bioavailability (F30%):	0.574

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.172
Plasma Protein Binding (PPB):	49.46277618408203%
Volume Distribution (VD):	0.758
Pgp-substrate:	54.726661682128906%

ADMET: Metabolism

CYP1A2-inhibitor:	0.004
CYP1A2-substrate:	0.551
CYP2C19-inhibitor:	0.008
CYP2C19-substrate:	0.649
CYP2C9-inhibitor:	0.018
CYP2C9-substrate:	0.062
CYP2D6-inhibitor:	0.003
CYP2D6-substrate:	0.086
CYP3A4-inhibitor:	0.747
CYP3A4-substrate:	0.282

ADMET: Excretion

Clearance (CL):	15.178
Half-life (T1/2):	0.837

ADMET: Toxicity

hERG Blockers:	0.035
Human Hepatotoxicity (H-HT):	0.115
Drug-inuced Liver Injury (DILI):	0.114
AMES Toxicity:	0.123
Rat Oral Acute Toxicity:	0.1
Maximum Recommended Daily Dose:	0.682
Skin Sensitization:	0.512
Carcinogencity:	0.312
Eye Corrosion:	0.008
Eye Irritation:	0.02
Respiratory Toxicity:	0.928

Download Data

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

Natural Product: NPC476812

Natural Product ID:	NPC476812
*Common Name:**	Tagalsin T
IUPAC Name:	(1Z,4aR,4bS,7S,8aS,10aS)-7-(1,2-dihydroxyethyl)-1-(hydroxymethylidene)-4b,7,10a-trimethyl-4,4a,5,6,8,8a,9,10-octahydro-3H-phenanthren-2-one
Synonyms:	Tagalsin T
Standard InCHIKey:	VEHQOXOBKPFBHP-HLVJOWEYSA-N
Standard InCHI:	InChI=1S/C20H32O4/c1-18(17(24)12-22)8-9-19(2)13(10-18)6-7-20(3)14(11-21)15(23)4-5-16(19)20/h11,13,16-17,21-22,24H,4-10,12H2,1-3H3/b14-11+/t13-,16+,17?,18-,19-,20+/m0/s1
SMILES:	C[C@@]1(CC[C@]2([C@H](C1)CC[C@]\3([C@@H]2CCC(=O)/C3=C\O)C)C)C(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	49831547
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001757] Colensane and clerodane diterpenoids

*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
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	fruits	n.a.	n.a.	PMID[16378377]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	stems and twigs	mangrove wetlands of Hainan Island, China	2002-JUL	PMID[20886837]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	stems and twigs	the mangrove wetlands of Hainan Island, China	2002-JUL	PMID[20886837]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19887	Ceriops tagal	Species	Rhizophoraceae	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	6

Activity Type	# Activity
Organism	6

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	-5	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	-11	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	-32	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	-20	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	-31	%	PMID[20886837]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	-48	%	PMID[20886837]

☑ 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 NPC476812 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	196
0.1-0.2	1655
0.2-0.3	6256
0.3-0.4	15705
0.4-0.5	7363
0.5-0.6	6192
0.6-0.7	4128
0.7-0.8	1160
0.8-0.85	34
0.85-0.9	4
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC149249
0.92	High Similarity	NPC476811
0.9079	High Similarity	NPC476810
0.8701	High Similarity	NPC106078
0.8519	High Similarity	NPC86370
0.8462	Intermediate Similarity	NPC472746
0.8395	Intermediate Similarity	NPC212083
0.8313	Intermediate Similarity	NPC76518
0.8293	Intermediate Similarity	NPC291320
0.8293	Intermediate Similarity	NPC118800
0.8293	Intermediate Similarity	NPC175410
0.8293	Intermediate Similarity	NPC471036
0.825	Intermediate Similarity	NPC201459
0.8214	Intermediate Similarity	NPC34190
0.8193	Intermediate Similarity	NPC146683
0.8193	Intermediate Similarity	NPC473157
0.8171	Intermediate Similarity	NPC145143
0.8171	Intermediate Similarity	NPC477858
0.8148	Intermediate Similarity	NPC2482
0.814	Intermediate Similarity	NPC469319
0.814	Intermediate Similarity	NPC229871
0.8118	Intermediate Similarity	NPC90652
0.8118	Intermediate Similarity	NPC153604
0.8118	Intermediate Similarity	NPC469317
0.8118	Intermediate Similarity	NPC469314
0.8118	Intermediate Similarity	NPC259009
0.8118	Intermediate Similarity	NPC241875
0.8118	Intermediate Similarity	NPC174619
0.8095	Intermediate Similarity	NPC190704
0.8095	Intermediate Similarity	NPC102292
0.8095	Intermediate Similarity	NPC471034
0.8072	Intermediate Similarity	NPC472743
0.8072	Intermediate Similarity	NPC475726
0.8049	Intermediate Similarity	NPC103754
0.8049	Intermediate Similarity	NPC474484
0.8049	Intermediate Similarity	NPC328264
0.8049	Intermediate Similarity	NPC3915
0.8023	Intermediate Similarity	NPC470417
0.8023	Intermediate Similarity	NPC472739
0.8	Intermediate Similarity	NPC325946
0.8	Intermediate Similarity	NPC471035
0.8	Intermediate Similarity	NPC158393
0.8	Intermediate Similarity	NPC473168
0.8	Intermediate Similarity	NPC98236
0.8	Intermediate Similarity	NPC70661
0.8	Intermediate Similarity	NPC269396
0.8	Intermediate Similarity	NPC324063
0.8	Intermediate Similarity	NPC212661
0.8	Intermediate Similarity	NPC473158
0.7978	Intermediate Similarity	NPC23170
0.7976	Intermediate Similarity	NPC474233
0.7976	Intermediate Similarity	NPC180834
0.7976	Intermediate Similarity	NPC85774
0.7976	Intermediate Similarity	NPC475745
0.7976	Intermediate Similarity	NPC130966
0.7976	Intermediate Similarity	NPC474482
0.7976	Intermediate Similarity	NPC214043
0.7955	Intermediate Similarity	NPC473167
0.7952	Intermediate Similarity	NPC103486
0.7952	Intermediate Similarity	NPC110780
0.7952	Intermediate Similarity	NPC310989
0.7952	Intermediate Similarity	NPC46881
0.7931	Intermediate Similarity	NPC220498
0.7931	Intermediate Similarity	NPC477973
0.7931	Intermediate Similarity	NPC32830
0.7931	Intermediate Similarity	NPC184663
0.7927	Intermediate Similarity	NPC164999
0.7927	Intermediate Similarity	NPC472478
0.7922	Intermediate Similarity	NPC91369
0.7907	Intermediate Similarity	NPC165895
0.7907	Intermediate Similarity	NPC469322
0.7907	Intermediate Similarity	NPC474174
0.7907	Intermediate Similarity	NPC93778
0.7907	Intermediate Similarity	NPC251808
0.7907	Intermediate Similarity	NPC99909
0.7889	Intermediate Similarity	NPC41070
0.7889	Intermediate Similarity	NPC142352
0.7882	Intermediate Similarity	NPC274724
0.7882	Intermediate Similarity	NPC133954
0.7882	Intermediate Similarity	NPC292553
0.7882	Intermediate Similarity	NPC201655
0.7867	Intermediate Similarity	NPC103734
0.7865	Intermediate Similarity	NPC474736
0.7865	Intermediate Similarity	NPC141447
0.7865	Intermediate Similarity	NPC294263
0.7865	Intermediate Similarity	NPC211230
0.7857	Intermediate Similarity	NPC471037
0.7857	Intermediate Similarity	NPC307258
0.7857	Intermediate Similarity	NPC245866
0.7857	Intermediate Similarity	NPC472498
0.7848	Intermediate Similarity	NPC162164
0.7848	Intermediate Similarity	NPC470299
0.7841	Intermediate Similarity	NPC261994
0.7841	Intermediate Similarity	NPC126993
0.7841	Intermediate Similarity	NPC85173
0.7841	Intermediate Similarity	NPC80401
0.7841	Intermediate Similarity	NPC49320
0.7841	Intermediate Similarity	NPC470378
0.7841	Intermediate Similarity	NPC149761
0.7841	Intermediate Similarity	NPC180849
0.7831	Intermediate Similarity	NPC116797
0.7831	Intermediate Similarity	NPC278459
0.7831	Intermediate Similarity	NPC121984
0.7831	Intermediate Similarity	NPC473217
0.7816	Intermediate Similarity	NPC230387
0.7816	Intermediate Similarity	NPC44181
0.7816	Intermediate Similarity	NPC206060
0.7816	Intermediate Similarity	NPC255176
0.7816	Intermediate Similarity	NPC474677
0.7816	Intermediate Similarity	NPC474719
0.7816	Intermediate Similarity	NPC472802
0.7816	Intermediate Similarity	NPC158778
0.7805	Intermediate Similarity	NPC471475
0.7805	Intermediate Similarity	NPC472490
0.7805	Intermediate Similarity	NPC474113
0.7802	Intermediate Similarity	NPC104568
0.7791	Intermediate Similarity	NPC80590
0.7791	Intermediate Similarity	NPC145879
0.7791	Intermediate Similarity	NPC56588
0.7791	Intermediate Similarity	NPC187545
0.7791	Intermediate Similarity	NPC179591
0.7791	Intermediate Similarity	NPC213412
0.7791	Intermediate Similarity	NPC31564
0.7791	Intermediate Similarity	NPC475862
0.7791	Intermediate Similarity	NPC471737
0.7791	Intermediate Similarity	NPC472738
0.7791	Intermediate Similarity	NPC474733
0.7791	Intermediate Similarity	NPC74363
0.7791	Intermediate Similarity	NPC322159
0.7791	Intermediate Similarity	NPC475007
0.7791	Intermediate Similarity	NPC474732
0.7791	Intermediate Similarity	NPC474778
0.7791	Intermediate Similarity	NPC2783
0.7791	Intermediate Similarity	NPC89077
0.7778	Intermediate Similarity	NPC474433
0.7778	Intermediate Similarity	NPC169751
0.7778	Intermediate Similarity	NPC472976
0.7778	Intermediate Similarity	NPC47853
0.7778	Intermediate Similarity	NPC264602
0.7778	Intermediate Similarity	NPC473172
0.7778	Intermediate Similarity	NPC474882
0.7778	Intermediate Similarity	NPC472977
0.7778	Intermediate Similarity	NPC272635
0.7765	Intermediate Similarity	NPC82902
0.7765	Intermediate Similarity	NPC329043
0.7765	Intermediate Similarity	NPC476412
0.7765	Intermediate Similarity	NPC227132
0.7765	Intermediate Similarity	NPC74595
0.7765	Intermediate Similarity	NPC161423
0.7765	Intermediate Similarity	NPC227064
0.7765	Intermediate Similarity	NPC263974
0.7765	Intermediate Similarity	NPC321187
0.7765	Intermediate Similarity	NPC58841
0.7765	Intermediate Similarity	NPC59453
0.7765	Intermediate Similarity	NPC264665
0.7765	Intermediate Similarity	NPC473246
0.7765	Intermediate Similarity	NPC221758
0.7753	Intermediate Similarity	NPC300351
0.7753	Intermediate Similarity	NPC272746
0.7753	Intermediate Similarity	NPC235884
0.7753	Intermediate Similarity	NPC473166
0.7753	Intermediate Similarity	NPC211403
0.7753	Intermediate Similarity	NPC84319
0.7753	Intermediate Similarity	NPC52021
0.7753	Intermediate Similarity	NPC25299
0.7753	Intermediate Similarity	NPC306541
0.7753	Intermediate Similarity	NPC476168
0.7753	Intermediate Similarity	NPC145067
0.7753	Intermediate Similarity	NPC299185
0.7753	Intermediate Similarity	NPC198242
0.7753	Intermediate Similarity	NPC155304
0.7753	Intermediate Similarity	NPC233455
0.7753	Intermediate Similarity	NPC71074
0.7753	Intermediate Similarity	NPC250753
0.7753	Intermediate Similarity	NPC4036
0.7753	Intermediate Similarity	NPC158030
0.7753	Intermediate Similarity	NPC472149
0.7753	Intermediate Similarity	NPC278106
0.7753	Intermediate Similarity	NPC65120
0.775	Intermediate Similarity	NPC114236
0.7738	Intermediate Similarity	NPC151519
0.7738	Intermediate Similarity	NPC48362
0.7738	Intermediate Similarity	NPC474605
0.7738	Intermediate Similarity	NPC170985
0.7738	Intermediate Similarity	NPC476292
0.7727	Intermediate Similarity	NPC250592
0.7727	Intermediate Similarity	NPC281524
0.7727	Intermediate Similarity	NPC477943
0.7727	Intermediate Similarity	NPC77263
0.7727	Intermediate Similarity	NPC1015
0.7727	Intermediate Similarity	NPC31985
0.7722	Intermediate Similarity	NPC81759
0.7722	Intermediate Similarity	NPC36310
0.7711	Intermediate Similarity	NPC18955
0.7701	Intermediate Similarity	NPC475740
0.7701	Intermediate Similarity	NPC73064
0.7701	Intermediate Similarity	NPC138756
0.7701	Intermediate Similarity	NPC58063
0.7701	Intermediate Similarity	NPC33768
0.7701	Intermediate Similarity	NPC472324

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 NPC476812 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	198
0.1-0.2	2131
0.2-0.3	3982
0.3-0.4	2011
0.4-0.5	423
0.5-0.6	202
0.6-0.7	169
0.7-0.8	33
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
0.8519	High Similarity	NPD4788	Approved
0.7765	Intermediate Similarity	NPD3133	Approved
0.7765	Intermediate Similarity	NPD3666	Approved
0.7765	Intermediate Similarity	NPD4786	Approved
0.7765	Intermediate Similarity	NPD3665	Phase 1
0.7753	Intermediate Similarity	NPD7515	Phase 2
0.7738	Intermediate Similarity	NPD3667	Approved
0.7711	Intermediate Similarity	NPD4695	Discontinued
0.7692	Intermediate Similarity	NPD4245	Approved
0.7692	Intermediate Similarity	NPD4244	Approved
0.7674	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3618	Phase 1
0.7564	Intermediate Similarity	NPD3698	Phase 2
0.7564	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7564	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD6079	Approved
0.7528	Intermediate Similarity	NPD5328	Approved
0.747	Intermediate Similarity	NPD3617	Approved
0.7468	Intermediate Similarity	NPD4789	Approved
0.7391	Intermediate Similarity	NPD7748	Approved
0.7333	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7333	Intermediate Similarity	NPD4753	Phase 2
0.7273	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7234	Intermediate Similarity	NPD5221	Approved
0.7234	Intermediate Similarity	NPD5222	Approved
0.7234	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD6117	Approved
0.7195	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7191	Intermediate Similarity	NPD5279	Phase 3
0.7191	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7174	Intermediate Similarity	NPD8035	Phase 2
0.7174	Intermediate Similarity	NPD8034	Phase 2
0.7159	Intermediate Similarity	NPD3668	Phase 3
0.7158	Intermediate Similarity	NPD5173	Approved
0.7158	Intermediate Similarity	NPD7902	Approved
0.7143	Intermediate Similarity	NPD6116	Phase 1
0.7128	Intermediate Similarity	NPD5210	Approved
0.7128	Intermediate Similarity	NPD4629	Approved
0.7126	Intermediate Similarity	NPD4223	Phase 3
0.7126	Intermediate Similarity	NPD4221	Approved
0.7108	Intermediate Similarity	NPD3703	Phase 2
0.7097	Intermediate Similarity	NPD6399	Phase 3
0.7097	Intermediate Similarity	NPD4202	Approved
0.7079	Intermediate Similarity	NPD5329	Approved
0.7059	Intermediate Similarity	NPD6114	Approved
0.7059	Intermediate Similarity	NPD6115	Approved
0.7059	Intermediate Similarity	NPD6118	Approved
0.7059	Intermediate Similarity	NPD6697	Approved
0.7053	Intermediate Similarity	NPD4697	Phase 3
0.7033	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD5286	Approved
0.701	Intermediate Similarity	NPD4696	Approved
0.701	Intermediate Similarity	NPD5285	Approved
0.7	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5330	Approved
0.7	Intermediate Similarity	NPD6409	Approved
0.7	Intermediate Similarity	NPD7334	Approved
0.7	Intermediate Similarity	NPD7146	Approved
0.7	Intermediate Similarity	NPD6684	Approved
0.7	Intermediate Similarity	NPD5360	Phase 3
0.7	Intermediate Similarity	NPD7521	Approved
0.6979	Remote Similarity	NPD4755	Approved
0.6979	Remote Similarity	NPD6083	Phase 2
0.6979	Remote Similarity	NPD6084	Phase 2
0.6966	Remote Similarity	NPD4197	Approved
0.6962	Remote Similarity	NPD4224	Phase 2
0.6951	Remote Similarity	NPD6081	Approved
0.6939	Remote Similarity	NPD5223	Approved
0.6931	Remote Similarity	NPD6412	Phase 2
0.6897	Remote Similarity	NPD7525	Registered
0.6875	Remote Similarity	NPD7614	Phase 1
0.6869	Remote Similarity	NPD5211	Phase 2
0.6869	Remote Similarity	NPD4633	Approved
0.6869	Remote Similarity	NPD5225	Approved
0.6869	Remote Similarity	NPD5224	Approved
0.6869	Remote Similarity	NPD5226	Approved
0.686	Remote Similarity	NPD3671	Phase 1
0.6848	Remote Similarity	NPD6672	Approved
0.6848	Remote Similarity	NPD6903	Approved
0.6848	Remote Similarity	NPD5737	Approved
0.6842	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6842	Remote Similarity	NPD7900	Approved
0.6837	Remote Similarity	NPD4700	Approved
0.6813	Remote Similarity	NPD4690	Approved
0.6813	Remote Similarity	NPD5690	Phase 2
0.6813	Remote Similarity	NPD5205	Approved
0.6813	Remote Similarity	NPD4693	Phase 3
0.6813	Remote Similarity	NPD4689	Approved
0.6813	Remote Similarity	NPD4519	Discontinued
0.6813	Remote Similarity	NPD4138	Approved
0.6813	Remote Similarity	NPD4688	Approved
0.6813	Remote Similarity	NPD4623	Approved
0.68	Remote Similarity	NPD5174	Approved
0.68	Remote Similarity	NPD5175	Approved
0.6782	Remote Similarity	NPD7645	Phase 2
0.6747	Remote Similarity	NPD5777	Approved
0.6735	Remote Similarity	NPD7638	Approved
0.6733	Remote Similarity	NPD5141	Approved
0.6731	Remote Similarity	NPD4634	Approved
0.6707	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7339	Approved
0.6706	Remote Similarity	NPD6942	Approved
0.6699	Remote Similarity	NPD6899	Approved
0.6699	Remote Similarity	NPD6686	Approved
0.6699	Remote Similarity	NPD6881	Approved
0.6667	Remote Similarity	NPD7128	Approved
0.6667	Remote Similarity	NPD5739	Approved
0.6667	Remote Similarity	NPD6402	Approved
0.6667	Remote Similarity	NPD6675	Approved
0.6667	Remote Similarity	NPD7640	Approved
0.6667	Remote Similarity	NPD7639	Approved
0.6634	Remote Similarity	NPD4754	Approved
0.663	Remote Similarity	NPD4694	Approved
0.663	Remote Similarity	NPD5280	Approved
0.6629	Remote Similarity	NPD4692	Approved
0.6629	Remote Similarity	NPD4139	Approved
0.6628	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6628	Remote Similarity	NPD6933	Approved
0.6627	Remote Similarity	NPD4691	Approved
0.6604	Remote Similarity	NPD8297	Approved
0.6602	Remote Similarity	NPD5697	Approved
0.6598	Remote Similarity	NPD5695	Phase 3
0.6591	Remote Similarity	NPD4195	Approved
0.6571	Remote Similarity	NPD7290	Approved
0.6571	Remote Similarity	NPD7102	Approved
0.6571	Remote Similarity	NPD6883	Approved
0.6566	Remote Similarity	NPD5696	Approved
0.6556	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6548	Remote Similarity	NPD4758	Discontinued
0.6542	Remote Similarity	NPD4632	Approved
0.6538	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD4729	Approved
0.6538	Remote Similarity	NPD4730	Approved
0.6538	Remote Similarity	NPD6011	Approved
0.6538	Remote Similarity	NPD7320	Approved
0.6538	Remote Similarity	NPD5168	Approved
0.6538	Remote Similarity	NPD5128	Approved
0.6531	Remote Similarity	NPD7732	Phase 3
0.6514	Remote Similarity	NPD7115	Discovery
0.6509	Remote Similarity	NPD6649	Approved
0.6509	Remote Similarity	NPD6869	Approved
0.6509	Remote Similarity	NPD6847	Approved
0.6509	Remote Similarity	NPD6617	Approved
0.6509	Remote Similarity	NPD6650	Approved
0.6509	Remote Similarity	NPD8130	Phase 1
0.6506	Remote Similarity	NPD4137	Phase 3
0.6505	Remote Similarity	NPD4767	Approved
0.6505	Remote Similarity	NPD4768	Approved
0.6477	Remote Similarity	NPD5364	Discontinued
0.6476	Remote Similarity	NPD6012	Approved
0.6476	Remote Similarity	NPD6013	Approved
0.6476	Remote Similarity	NPD6372	Approved
0.6476	Remote Similarity	NPD6014	Approved
0.6476	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD6373	Approved
0.6458	Remote Similarity	NPD5281	Approved
0.6458	Remote Similarity	NPD5284	Approved
0.6458	Remote Similarity	NPD6411	Approved
0.6449	Remote Similarity	NPD6882	Approved
0.6442	Remote Similarity	NPD5701	Approved
0.6429	Remote Similarity	NPD4747	Approved
0.6421	Remote Similarity	NPD6080	Approved
0.6421	Remote Similarity	NPD6904	Approved
0.6421	Remote Similarity	NPD6673	Approved
0.642	Remote Similarity	NPD7341	Phase 2
0.6415	Remote Similarity	NPD5251	Approved
0.6415	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6415	Remote Similarity	NPD5247	Approved
0.6415	Remote Similarity	NPD5248	Approved
0.6415	Remote Similarity	NPD5135	Approved
0.6415	Remote Similarity	NPD5249	Phase 3
0.6415	Remote Similarity	NPD5169	Approved
0.6415	Remote Similarity	NPD5250	Approved
0.64	Remote Similarity	NPD4225	Approved
0.6395	Remote Similarity	NPD6926	Approved
0.6395	Remote Similarity	NPD4058	Approved
0.6395	Remote Similarity	NPD6924	Approved
0.6389	Remote Similarity	NPD8133	Approved
0.6383	Remote Similarity	NPD3573	Approved
0.6373	Remote Similarity	NPD7632	Discontinued
0.6355	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5215	Approved
0.6355	Remote Similarity	NPD5216	Approved
0.6355	Remote Similarity	NPD5127	Approved
0.6355	Remote Similarity	NPD5217	Approved
0.6333	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6322	Remote Similarity	NPD3702	Approved
0.6321	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6292	Remote Similarity	NPD5784	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD6098	Approved
0.6273	Remote Similarity	NPD6868	Approved
0.6264	Remote Similarity	NPD8028	Phase 2
0.6263	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.625	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.625	Remote Similarity	NPD6101	Approved
0.625	Remote Similarity	NPD4522	Approved
0.6224	Remote Similarity	NPD5133	Approved
0.6216	Remote Similarity	NPD6009	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