NPASS Compound

Structure

CID149249 OpenBabel06191715522D 23 25 0 0 1 0 0 0 0 0999 V2000 -3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -1.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.7321 -1.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2321 -1.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2321 -0.1340 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 13 2 0 0 0 0 5 6 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 19 1 0 0 0 0 9 10 1 0 0 0 0 9 18 1 0 0 0 0 10 20 1 0 0 0 0 11 14 1 0 0 0 0 11 18 1 0 0 0 0 12 17 1 0 0 0 0 12 21 1 0 0 0 0 13 15 1 0 0 0 0 13 19 1 0 0 0 0 14 20 1 6 0 0 0 15 22 2 0 0 0 0 16 19 1 6 0 0 0 16 20 1 0 0 0 0 17 18 1 0 0 0 0 17 23 1 0 0 0 0 18 2 1 1 0 0 0 19 3 1 1 0 0 0 20 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	320.24
Volume:	349.905
LogP:	2.65
LogD:	2.484
LogS:	-2.855
# Rotatable Bonds:	2
TPSA:	57.53
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.766
Synthetic Accessibility Score:	4.744
Fsp3:	0.85
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	2
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.818
MDCK Permeability:	9.27584187593311e-06
Pgp-inhibitor:	0.032
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.008

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.342
Plasma Protein Binding (PPB):	70.51559448242188%
Volume Distribution (VD):	0.529
Pgp-substrate:	27.188148498535156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.014
CYP1A2-substrate:	0.621
CYP2C19-inhibitor:	0.022
CYP2C19-substrate:	0.824
CYP2C9-inhibitor:	0.044
CYP2C9-substrate:	0.049
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.081
CYP3A4-inhibitor:	0.735
CYP3A4-substrate:	0.4

ADMET: Excretion

Clearance (CL):	15.253
Half-life (T1/2):	0.436

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.676
Drug-inuced Liver Injury (DILI):	0.155
AMES Toxicity:	0.093
Rat Oral Acute Toxicity:	0.592
Maximum Recommended Daily Dose:	0.774
Skin Sensitization:	0.781
Carcinogencity:	0.923
Eye Corrosion:	0.006
Eye Irritation:	0.02
Respiratory Toxicity:	0.974

Download Data

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

Natural Product: NPC149249

Natural Product ID:	NPC149249
*Common Name:**	Tagalsin U
IUPAC Name:	(4aR,4bS,7S,8aS,10aS)-7-(1,2-dihydroxyethyl)-4b,7,10a-trimethyl-1-methylidene-4,4a,5,6,8,8a,9,10-octahydro-3H-phenanthren-2-one
Synonyms:	Tagalsin U
Standard InCHIKey:	IEFOVVVAKRWGFT-PHJAUKBRSA-N
Standard InCHI:	InChI=1S/C20H32O3/c1-13-15(22)5-6-16-19(13,3)8-7-14-11-18(2,17(23)12-21)9-10-20(14,16)4/h14,16-17,21,23H,1,5-12H2,2-4H3/t14-,16-,17?,18-,19+,20-/m0/s1
SMILES:	C=C1C(=O)CC[C@H]2[C@]1(C)CC[C@H]1C[C@](C)(CC[C@]21C)C(CO)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1269830
PubChem CID:	49831548
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	=	52.0	%	PMID[533248]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	41.0	%	PMID[533248]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	14.0	%	PMID[533248]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	31.0	%	PMID[533248]
NPT4696	Organism	Brontispa longissima	Brontispa longissima	Activity	=	10.0	%	PMID[533248]

☑ 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 NPC149249 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	193
0.1-0.2	1698
0.2-0.3	6925
0.3-0.4	15775
0.4-0.5	6866
0.5-0.6	5963
0.6-0.7	3990
0.7-0.8	1223
0.8-0.85	54
0.85-0.9	7
0.9-0.95	1
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9726	High Similarity	NPC476812
0.8933	High Similarity	NPC476811
0.8933	High Similarity	NPC106078
0.8816	High Similarity	NPC476810
0.8684	High Similarity	NPC472746
0.8519	High Similarity	NPC76518
0.85	High Similarity	NPC118800
0.85	High Similarity	NPC291320
0.85	High Similarity	NPC175410
0.85	High Similarity	NPC471036
0.85	High Similarity	NPC86370
0.8462	Intermediate Similarity	NPC201459
0.8395	Intermediate Similarity	NPC473157
0.8395	Intermediate Similarity	NPC146683
0.8375	Intermediate Similarity	NPC477858
0.8375	Intermediate Similarity	NPC145143
0.8375	Intermediate Similarity	NPC212083
0.8354	Intermediate Similarity	NPC2482
0.8293	Intermediate Similarity	NPC102292
0.8293	Intermediate Similarity	NPC471034
0.8293	Intermediate Similarity	NPC190704
0.8272	Intermediate Similarity	NPC475726
0.8272	Intermediate Similarity	NPC472743
0.825	Intermediate Similarity	NPC328264
0.825	Intermediate Similarity	NPC3915
0.825	Intermediate Similarity	NPC474484
0.825	Intermediate Similarity	NPC103754
0.8214	Intermediate Similarity	NPC472739
0.8205	Intermediate Similarity	NPC212661
0.8205	Intermediate Similarity	NPC325946
0.8205	Intermediate Similarity	NPC471035
0.8193	Intermediate Similarity	NPC98236
0.8193	Intermediate Similarity	NPC269396
0.8193	Intermediate Similarity	NPC34190
0.8193	Intermediate Similarity	NPC473168
0.8193	Intermediate Similarity	NPC158393
0.8171	Intermediate Similarity	NPC85774
0.8171	Intermediate Similarity	NPC474233
0.8171	Intermediate Similarity	NPC180834
0.8171	Intermediate Similarity	NPC474482
0.8171	Intermediate Similarity	NPC475745
0.8171	Intermediate Similarity	NPC214043
0.8148	Intermediate Similarity	NPC46881
0.8148	Intermediate Similarity	NPC310989
0.8148	Intermediate Similarity	NPC110780
0.8133	Intermediate Similarity	NPC91369
0.8125	Intermediate Similarity	NPC164999
0.8125	Intermediate Similarity	NPC472478
0.8118	Intermediate Similarity	NPC469319
0.8118	Intermediate Similarity	NPC229871
0.8095	Intermediate Similarity	NPC165895
0.8095	Intermediate Similarity	NPC469322
0.8095	Intermediate Similarity	NPC93778
0.8095	Intermediate Similarity	NPC174619
0.8095	Intermediate Similarity	NPC90652
0.8095	Intermediate Similarity	NPC469317
0.8095	Intermediate Similarity	NPC469314
0.8095	Intermediate Similarity	NPC259009
0.8095	Intermediate Similarity	NPC241875
0.8095	Intermediate Similarity	NPC153604
0.8082	Intermediate Similarity	NPC103734
0.8072	Intermediate Similarity	NPC274724
0.8072	Intermediate Similarity	NPC133954
0.8072	Intermediate Similarity	NPC292553
0.8052	Intermediate Similarity	NPC470299
0.8052	Intermediate Similarity	NPC162164
0.8049	Intermediate Similarity	NPC307258
0.8049	Intermediate Similarity	NPC245866
0.8049	Intermediate Similarity	NPC472498
0.8046	Intermediate Similarity	NPC474736
0.8025	Intermediate Similarity	NPC473217
0.8025	Intermediate Similarity	NPC121984
0.8023	Intermediate Similarity	NPC85173
0.8023	Intermediate Similarity	NPC126993
0.8	Intermediate Similarity	NPC474113
0.8	Intermediate Similarity	NPC472490
0.8	Intermediate Similarity	NPC471475
0.8	Intermediate Similarity	NPC158778
0.8	Intermediate Similarity	NPC206060
0.8	Intermediate Similarity	NPC472802
0.8	Intermediate Similarity	NPC470417
0.8	Intermediate Similarity	NPC474677
0.7978	Intermediate Similarity	NPC473158
0.7976	Intermediate Similarity	NPC31564
0.7976	Intermediate Similarity	NPC179591
0.7976	Intermediate Similarity	NPC474733
0.7976	Intermediate Similarity	NPC213412
0.7976	Intermediate Similarity	NPC324063
0.7976	Intermediate Similarity	NPC89077
0.7976	Intermediate Similarity	NPC472738
0.7976	Intermediate Similarity	NPC70661
0.7976	Intermediate Similarity	NPC74363
0.7976	Intermediate Similarity	NPC474732
0.7976	Intermediate Similarity	NPC471737
0.7976	Intermediate Similarity	NPC474778
0.7976	Intermediate Similarity	NPC145879
0.7976	Intermediate Similarity	NPC475862
0.7952	Intermediate Similarity	NPC82902
0.7952	Intermediate Similarity	NPC263974
0.7952	Intermediate Similarity	NPC227132
0.7952	Intermediate Similarity	NPC161423
0.7952	Intermediate Similarity	NPC329043
0.7952	Intermediate Similarity	NPC227064
0.7952	Intermediate Similarity	NPC130966
0.7952	Intermediate Similarity	NPC476412
0.7952	Intermediate Similarity	NPC58841
0.7952	Intermediate Similarity	NPC473246
0.7952	Intermediate Similarity	NPC74595
0.7952	Intermediate Similarity	NPC321187
0.7952	Intermediate Similarity	NPC264665
0.7952	Intermediate Similarity	NPC59453
0.7952	Intermediate Similarity	NPC221758
0.7949	Intermediate Similarity	NPC114236
0.7931	Intermediate Similarity	NPC272746
0.7931	Intermediate Similarity	NPC473167
0.7927	Intermediate Similarity	NPC151519
0.7927	Intermediate Similarity	NPC48362
0.7927	Intermediate Similarity	NPC170985
0.7922	Intermediate Similarity	NPC36310
0.7922	Intermediate Similarity	NPC81759
0.7907	Intermediate Similarity	NPC477973
0.7907	Intermediate Similarity	NPC32830
0.7907	Intermediate Similarity	NPC184663
0.7907	Intermediate Similarity	NPC220498
0.7882	Intermediate Similarity	NPC475740
0.7882	Intermediate Similarity	NPC4643
0.7882	Intermediate Similarity	NPC251808
0.7882	Intermediate Similarity	NPC58063
0.7882	Intermediate Similarity	NPC474174
0.7882	Intermediate Similarity	NPC57469
0.7882	Intermediate Similarity	NPC99909
0.7882	Intermediate Similarity	NPC73064
0.7867	Intermediate Similarity	NPC474954
0.7867	Intermediate Similarity	NPC260319
0.7867	Intermediate Similarity	NPC180777
0.7867	Intermediate Similarity	NPC103647
0.7867	Intermediate Similarity	NPC2568
0.7865	Intermediate Similarity	NPC41070
0.7865	Intermediate Similarity	NPC142352
0.7857	Intermediate Similarity	NPC476426
0.7857	Intermediate Similarity	NPC471224
0.7857	Intermediate Similarity	NPC201655
0.7857	Intermediate Similarity	NPC264317
0.7857	Intermediate Similarity	NPC474218
0.7857	Intermediate Similarity	NPC294438
0.7857	Intermediate Similarity	NPC469948
0.7857	Intermediate Similarity	NPC470574
0.7841	Intermediate Similarity	NPC294263
0.7841	Intermediate Similarity	NPC109305
0.7831	Intermediate Similarity	NPC472740
0.7831	Intermediate Similarity	NPC471037
0.7821	Intermediate Similarity	NPC38426
0.7821	Intermediate Similarity	NPC472854
0.7816	Intermediate Similarity	NPC149761
0.7816	Intermediate Similarity	NPC261994
0.7816	Intermediate Similarity	NPC470378
0.7816	Intermediate Similarity	NPC180849
0.7816	Intermediate Similarity	NPC49320
0.7816	Intermediate Similarity	NPC80401
0.7805	Intermediate Similarity	NPC471898
0.7805	Intermediate Similarity	NPC116797
0.7805	Intermediate Similarity	NPC278459
0.7805	Intermediate Similarity	NPC14151
0.7792	Intermediate Similarity	NPC156277
0.7792	Intermediate Similarity	NPC72343
0.7792	Intermediate Similarity	NPC151018
0.7792	Intermediate Similarity	NPC58057
0.7792	Intermediate Similarity	NPC320549
0.7791	Intermediate Similarity	NPC255176
0.7791	Intermediate Similarity	NPC44181
0.7791	Intermediate Similarity	NPC474925
0.7791	Intermediate Similarity	NPC474719
0.7791	Intermediate Similarity	NPC193360
0.7791	Intermediate Similarity	NPC230387
0.7791	Intermediate Similarity	NPC471724
0.7778	Intermediate Similarity	NPC104568
0.7778	Intermediate Similarity	NPC215843
0.7778	Intermediate Similarity	NPC192744
0.7765	Intermediate Similarity	NPC95594
0.7765	Intermediate Similarity	NPC72133
0.7765	Intermediate Similarity	NPC56588
0.7765	Intermediate Similarity	NPC94666
0.7765	Intermediate Similarity	NPC477579
0.7765	Intermediate Similarity	NPC51014
0.7765	Intermediate Similarity	NPC327115
0.7765	Intermediate Similarity	NPC2783
0.7765	Intermediate Similarity	NPC12774
0.7765	Intermediate Similarity	NPC187545
0.7765	Intermediate Similarity	NPC469994
0.7765	Intermediate Similarity	NPC80590
0.7765	Intermediate Similarity	NPC470955
0.7765	Intermediate Similarity	NPC72638
0.7765	Intermediate Similarity	NPC475007
0.7765	Intermediate Similarity	NPC235341
0.7765	Intermediate Similarity	NPC322159
0.7763	Intermediate Similarity	NPC324607
0.7763	Intermediate Similarity	NPC131892
0.7763	Intermediate Similarity	NPC327728
0.7763	Intermediate Similarity	NPC321732
0.7763	Intermediate Similarity	NPC213178

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 NPC149249 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	201
0.1-0.2	2243
0.2-0.3	4034
0.3-0.4	1858
0.4-0.5	420
0.5-0.6	189
0.6-0.7	164
0.7-0.8	40
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
0.85	High Similarity	NPD4788	Approved
0.7952	Intermediate Similarity	NPD3133	Approved
0.7952	Intermediate Similarity	NPD3666	Approved
0.7952	Intermediate Similarity	NPD3665	Phase 1
0.7952	Intermediate Similarity	NPD4786	Approved
0.7927	Intermediate Similarity	NPD3667	Approved
0.7895	Intermediate Similarity	NPD4245	Approved
0.7895	Intermediate Similarity	NPD4244	Approved
0.7857	Intermediate Similarity	NPD7520	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4808	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD4809	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD3618	Phase 1
0.7763	Intermediate Similarity	NPD3700	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3699	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD3698	Phase 2
0.7727	Intermediate Similarity	NPD7515	Phase 2
0.7727	Intermediate Similarity	NPD6079	Approved
0.7701	Intermediate Similarity	NPD5328	Approved
0.7662	Intermediate Similarity	NPD4789	Approved
0.747	Intermediate Similarity	NPD4695	Discontinued
0.7467	Intermediate Similarity	NPD3171	Clinical (unspecified phase)
0.7439	Intermediate Similarity	NPD3617	Approved
0.7375	Intermediate Similarity	NPD6113	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD7748	Approved
0.7356	Intermediate Similarity	NPD5279	Phase 3
0.7303	Intermediate Similarity	NPD4753	Phase 2
0.7294	Intermediate Similarity	NPD4221	Approved
0.7294	Intermediate Similarity	NPD4223	Phase 3
0.7284	Intermediate Similarity	NPD3703	Phase 2
0.7253	Intermediate Similarity	NPD4202	Approved
0.7241	Intermediate Similarity	NPD5329	Approved
0.7204	Intermediate Similarity	NPD5220	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5221	Approved
0.7204	Intermediate Similarity	NPD5222	Approved
0.7195	Intermediate Similarity	NPD6117	Approved
0.7191	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5361	Clinical (unspecified phase)
0.7179	Intermediate Similarity	NPD5360	Phase 3
0.7159	Intermediate Similarity	NPD6684	Approved
0.7159	Intermediate Similarity	NPD7521	Approved
0.7159	Intermediate Similarity	NPD7146	Approved
0.7159	Intermediate Similarity	NPD7334	Approved
0.7159	Intermediate Similarity	NPD6409	Approved
0.7159	Intermediate Similarity	NPD3574	Clinical (unspecified phase)
0.7159	Intermediate Similarity	NPD5330	Approved
0.7143	Intermediate Similarity	NPD8034	Phase 2
0.7143	Intermediate Similarity	NPD8035	Phase 2
0.7143	Intermediate Similarity	NPD4224	Phase 2
0.7128	Intermediate Similarity	NPD7902	Approved
0.7128	Intermediate Similarity	NPD5173	Approved
0.7126	Intermediate Similarity	NPD4197	Approved
0.7126	Intermediate Similarity	NPD3668	Phase 3
0.7111	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD6116	Phase 1
0.7097	Intermediate Similarity	NPD5210	Approved
0.7097	Intermediate Similarity	NPD4629	Approved
0.7065	Intermediate Similarity	NPD6399	Phase 3
0.7024	Intermediate Similarity	NPD6118	Approved
0.7024	Intermediate Similarity	NPD6114	Approved
0.7024	Intermediate Similarity	NPD3671	Phase 1
0.7024	Intermediate Similarity	NPD6115	Approved
0.7024	Intermediate Similarity	NPD6697	Approved
0.7021	Intermediate Similarity	NPD4697	Phase 3
0.7	Intermediate Similarity	NPD6903	Approved
0.6979	Remote Similarity	NPD5286	Approved
0.6979	Remote Similarity	NPD4696	Approved
0.6979	Remote Similarity	NPD5285	Approved
0.6966	Remote Similarity	NPD5690	Phase 2
0.6966	Remote Similarity	NPD5205	Approved
0.6966	Remote Similarity	NPD4623	Approved
0.6966	Remote Similarity	NPD4138	Approved
0.6966	Remote Similarity	NPD4689	Approved
0.6966	Remote Similarity	NPD4693	Phase 3
0.6966	Remote Similarity	NPD4688	Approved
0.6966	Remote Similarity	NPD4519	Discontinued
0.6966	Remote Similarity	NPD4690	Approved
0.6947	Remote Similarity	NPD4755	Approved
0.6947	Remote Similarity	NPD6083	Phase 2
0.6947	Remote Similarity	NPD6084	Phase 2
0.6941	Remote Similarity	NPD7645	Phase 2
0.6914	Remote Similarity	NPD6081	Approved
0.6914	Remote Similarity	NPD5777	Approved
0.6907	Remote Similarity	NPD5223	Approved
0.69	Remote Similarity	NPD6412	Phase 2
0.6867	Remote Similarity	NPD7339	Approved
0.6867	Remote Similarity	NPD6942	Approved
0.686	Remote Similarity	NPD7525	Registered
0.6842	Remote Similarity	NPD7614	Phase 1
0.6837	Remote Similarity	NPD5211	Phase 2
0.6837	Remote Similarity	NPD5224	Approved
0.6837	Remote Similarity	NPD5226	Approved
0.6837	Remote Similarity	NPD4633	Approved
0.6837	Remote Similarity	NPD5225	Approved
0.6813	Remote Similarity	NPD5737	Approved
0.6813	Remote Similarity	NPD6672	Approved
0.6809	Remote Similarity	NPD7900	Approved
0.6809	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6804	Remote Similarity	NPD4700	Approved
0.679	Remote Similarity	NPD4691	Approved
0.6786	Remote Similarity	NPD6933	Approved
0.6786	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD4692	Approved
0.6782	Remote Similarity	NPD4139	Approved
0.6778	Remote Similarity	NPD5280	Approved
0.6778	Remote Similarity	NPD4694	Approved
0.6768	Remote Similarity	NPD5174	Approved
0.6768	Remote Similarity	NPD5175	Approved
0.6744	Remote Similarity	NPD4195	Approved
0.6707	Remote Similarity	NPD4758	Discontinued
0.6701	Remote Similarity	NPD7638	Approved
0.67	Remote Similarity	NPD5141	Approved
0.6699	Remote Similarity	NPD4634	Approved
0.6667	Remote Similarity	NPD4137	Phase 3
0.6667	Remote Similarity	NPD4267	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6899	Approved
0.6667	Remote Similarity	NPD6686	Approved
0.6667	Remote Similarity	NPD6881	Approved
0.6634	Remote Similarity	NPD6675	Approved
0.6634	Remote Similarity	NPD6402	Approved
0.6634	Remote Similarity	NPD7128	Approved
0.6634	Remote Similarity	NPD5739	Approved
0.6633	Remote Similarity	NPD7640	Approved
0.6633	Remote Similarity	NPD7639	Approved
0.66	Remote Similarity	NPD4754	Approved
0.6585	Remote Similarity	NPD4747	Approved
0.6582	Remote Similarity	NPD7341	Phase 2
0.6571	Remote Similarity	NPD8297	Approved
0.6569	Remote Similarity	NPD5697	Approved
0.6562	Remote Similarity	NPD5695	Phase 3
0.6548	Remote Similarity	NPD6924	Approved
0.6548	Remote Similarity	NPD6926	Approved
0.6548	Remote Similarity	NPD4058	Approved
0.6538	Remote Similarity	NPD6883	Approved
0.6538	Remote Similarity	NPD7102	Approved
0.6538	Remote Similarity	NPD7290	Approved
0.6531	Remote Similarity	NPD5696	Approved
0.6522	Remote Similarity	NPD3573	Approved
0.6517	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6509	Remote Similarity	NPD4632	Approved
0.6505	Remote Similarity	NPD4729	Approved
0.6505	Remote Similarity	NPD5345	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4730	Approved
0.6505	Remote Similarity	NPD5128	Approved
0.6505	Remote Similarity	NPD6011	Approved
0.6505	Remote Similarity	NPD7320	Approved
0.6505	Remote Similarity	NPD5168	Approved
0.6495	Remote Similarity	NPD7732	Phase 3
0.6481	Remote Similarity	NPD7115	Discovery
0.6476	Remote Similarity	NPD6617	Approved
0.6476	Remote Similarity	NPD6650	Approved
0.6476	Remote Similarity	NPD6847	Approved
0.6476	Remote Similarity	NPD6649	Approved
0.6476	Remote Similarity	NPD6869	Approved
0.6476	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD4767	Approved
0.6471	Remote Similarity	NPD4768	Approved
0.6471	Remote Similarity	NPD3702	Approved
0.6442	Remote Similarity	NPD6014	Approved
0.6442	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6442	Remote Similarity	NPD6013	Approved
0.6442	Remote Similarity	NPD6372	Approved
0.6442	Remote Similarity	NPD6373	Approved
0.6442	Remote Similarity	NPD6012	Approved
0.6437	Remote Similarity	NPD5364	Discontinued
0.6421	Remote Similarity	NPD5281	Approved
0.6421	Remote Similarity	NPD5284	Approved
0.6421	Remote Similarity	NPD6411	Approved
0.6415	Remote Similarity	NPD6882	Approved
0.6413	Remote Similarity	NPD6098	Approved
0.6408	Remote Similarity	NPD5701	Approved
0.6404	Remote Similarity	NPD8028	Phase 2
0.6383	Remote Similarity	NPD6904	Approved
0.6383	Remote Similarity	NPD6673	Approved
0.6383	Remote Similarity	NPD6080	Approved
0.6381	Remote Similarity	NPD5134	Clinical (unspecified phase)
0.6381	Remote Similarity	NPD5248	Approved
0.6381	Remote Similarity	NPD5249	Phase 3
0.6381	Remote Similarity	NPD5135	Approved
0.6381	Remote Similarity	NPD5247	Approved
0.6381	Remote Similarity	NPD5251	Approved
0.6381	Remote Similarity	NPD5250	Approved
0.6381	Remote Similarity	NPD5169	Approved
0.6364	Remote Similarity	NPD4225	Approved
0.6355	Remote Similarity	NPD8133	Approved
0.6354	Remote Similarity	NPD5133	Approved
0.6353	Remote Similarity	NPD5733	Approved
0.6341	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD7632	Discontinued
0.6321	Remote Similarity	NPD5217	Approved
0.6321	Remote Similarity	NPD5216	Approved
0.6321	Remote Similarity	NPD5127	Approved
0.6321	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6321	Remote Similarity	NPD5215	Approved
0.6316	Remote Similarity	NPD4096	Approved
0.631	Remote Similarity	NPD4243	Approved
0.6304	Remote Similarity	NPD1694	Approved
0.6296	Remote Similarity	NPD7331	Phase 2
0.6292	Remote Similarity	NPD8259	Clinical (unspecified phase)
0.6286	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6277	Remote Similarity	NPD5208	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