NPASS Compound

Structure

CID2709 OpenBabel06191715322D 30 33 0 0 1 0 0 0 0 0999 V2000 -2.9873 3.6213 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0579 1.8827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 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 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -0.5000 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 3.4641 0.0000 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 -0.8660 -0.5000 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 5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5731 2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2462 2.6554 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 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 2.5981 -0.5000 0.0000 C 0 0 1 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 3.4641 -2.0000 0.0000 C 0 0 1 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 -0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2121 2.3966 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5391 1.9483 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 5 11 1 0 0 0 0 5 12 1 0 0 0 0 6 8 1 0 0 0 0 6 18 2 0 0 0 0 7 9 1 0 0 0 0 7 19 2 0 0 0 0 8 20 1 0 0 0 0 9 23 1 0 0 0 0 10 13 1 0 0 0 0 10 21 1 0 0 0 0 11 24 1 0 0 0 0 12 26 1 0 0 0 0 13 25 1 0 0 0 0 14 18 1 0 0 0 0 14 27 2 0 0 0 0 15 22 1 0 0 0 0 15 28 2 0 0 0 0 16 24 1 0 0 0 0 16 30 1 0 0 0 0 17 29 2 0 0 0 0 17 30 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 25 1 6 0 0 0 21 26 1 6 0 0 0 22 25 1 6 0 0 0 23 24 1 6 0 0 0 23 26 1 0 0 0 0 24 2 1 1 0 0 0 25 3 1 6 0 0 0 26 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	412.26
Volume:	446.005
LogP:	3.877
LogD:	3.754
LogS:	-4.656
# Rotatable Bonds:	5
TPSA:	60.44
# H-Bond Aceptor:	4
# H-Bond Donor:	0
# Rings:	4
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.367
Synthetic Accessibility Score:	4.901
Fsp3:	0.731
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:	-4.896
MDCK Permeability:	2.1841142370249145e-05
Pgp-inhibitor:	0.069
Pgp-substrate:	0.002
Human Intestinal Absorption (HIA):	0.04
20% Bioavailability (F20%):	0.935
30% Bioavailability (F30%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.33
Plasma Protein Binding (PPB):	67.29727935791016%
Volume Distribution (VD):	2.326
Pgp-substrate:	20.6779842376709%

ADMET: Metabolism

CYP1A2-inhibitor:	0.019
CYP1A2-substrate:	0.24
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.624
CYP2C9-inhibitor:	0.068
CYP2C9-substrate:	0.035
CYP2D6-inhibitor:	0.018
CYP2D6-substrate:	0.071
CYP3A4-inhibitor:	0.855
CYP3A4-substrate:	0.405

ADMET: Excretion

Clearance (CL):	2.632
Half-life (T1/2):	0.393

ADMET: Toxicity

hERG Blockers:	0.014
Human Hepatotoxicity (H-HT):	0.326
Drug-inuced Liver Injury (DILI):	0.048
AMES Toxicity:	0.026
Rat Oral Acute Toxicity:	0.006
Maximum Recommended Daily Dose:	0.917
Skin Sensitization:	0.955
Carcinogencity:	0.047
Eye Corrosion:	0.952
Eye Irritation:	0.928
Respiratory Toxicity:	0.979

Download Data

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

Natural Product: NPC2709

Natural Product ID:	NPC2709
*Common Name:**	Mooloolabene C
IUPAC Name:	[(1S,4aR,4bR,6aS,7R,10aR,12aR)-7,8-diformyl-1,4a,6a-trimethyl-3,4,4b,5,6,7,10,10a,12,12a-decahydro-2H-chrysen-1-yl]methyl acetate
Synonyms:	Mooloolabene C
Standard InCHIKey:	TYAAQNFJICIASZ-XGWBYYDQSA-N
Standard InCHI:	InChI=1S/C26H36O4/c1-17(29)30-16-24(2)11-5-12-26(4)21-10-13-25(3)20(19(21)7-9-23(24)26)8-6-18(14-27)22(25)15-28/h6-7,14-15,20-23H,5,8-13,16H2,1-4H3/t20-,21-,22-,23-,24+,25-,26+/m0/s1
SMILES:	CC(=O)OC[C@@]1(C)CCC[C@]2(C)[C@H]3CC[C@@]4(C)[C@@H](CC=C(C=O)[C@@H]4C=O)C3=CC[C@@H]12
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469398
PubChem CID:	11994177
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] 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
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	Inner Gneerings, a group of shoals off Mooloolaba (Australia)	2005-JUL	PMID[17125226]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[21608987]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7153777]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17690	Sideritis sventenii	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20034	Hyattella intestinalis	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18198	Selaginella willdenowii	Species	Selaginellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21592	Urtica circularis	Species	Urticaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19439	Calea zacatechichi	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21265	Teucrium webbianum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19595	Lathyrus chloranthus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16397	Didymocarpus oblonga	Species	Gesneriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12814	Daphne retusa	Species	Thymelaeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19293	Tabebuia cassinoides	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19735	Euonymus pellucidifolius	Species	Celastraceae	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
IC50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT168	Cell Line	P388	Mus musculus	IC50	=	3.0	ug.mL-1	PMID[460903]

☑ 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 NPC2709 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	205
0.1-0.2	1495
0.2-0.3	6086
0.3-0.4	14959
0.4-0.5	8072
0.5-0.6	6711
0.6-0.7	4049
0.7-0.8	1068
0.8-0.85	38
0.85-0.9	13
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9176	High Similarity	NPC101651
0.9176	High Similarity	NPC159748
0.9059	High Similarity	NPC469546
0.8966	High Similarity	NPC151722
0.8864	High Similarity	NPC269729
0.8764	High Similarity	NPC274417
0.8736	High Similarity	NPC328141
0.8675	High Similarity	NPC142683
0.8659	High Similarity	NPC474956
0.8642	High Similarity	NPC4827
0.8636	High Similarity	NPC230064
0.8608	High Similarity	NPC219232
0.8608	High Similarity	NPC128346
0.8571	High Similarity	NPC307258
0.8519	High Similarity	NPC472300
0.8434	Intermediate Similarity	NPC104545
0.8415	Intermediate Similarity	NPC59436
0.8409	Intermediate Similarity	NPC477973
0.8395	Intermediate Similarity	NPC899
0.8387	Intermediate Similarity	NPC475202
0.8387	Intermediate Similarity	NPC475392
0.8387	Intermediate Similarity	NPC475385
0.8375	Intermediate Similarity	NPC166797
0.8375	Intermediate Similarity	NPC211641
0.8333	Intermediate Similarity	NPC278459
0.8333	Intermediate Similarity	NPC474185
0.8333	Intermediate Similarity	NPC90055
0.8313	Intermediate Similarity	NPC327674
0.8295	Intermediate Similarity	NPC224145
0.8276	Intermediate Similarity	NPC195640
0.8256	Intermediate Similarity	NPC312660
0.8235	Intermediate Similarity	NPC200513
0.8222	Intermediate Similarity	NPC218301
0.8214	Intermediate Similarity	NPC267517
0.8214	Intermediate Similarity	NPC477057
0.8202	Intermediate Similarity	NPC184663
0.8193	Intermediate Similarity	NPC260385
0.8193	Intermediate Similarity	NPC110094
0.8193	Intermediate Similarity	NPC280654
0.8182	Intermediate Similarity	NPC477228
0.8182	Intermediate Similarity	NPC46912
0.8182	Intermediate Similarity	NPC162107
0.8161	Intermediate Similarity	NPC133652
0.8161	Intermediate Similarity	NPC189311
0.8161	Intermediate Similarity	NPC323765
0.8161	Intermediate Similarity	NPC474537
0.8148	Intermediate Similarity	NPC306928
0.814	Intermediate Similarity	NPC200752
0.8132	Intermediate Similarity	NPC476416
0.8125	Intermediate Similarity	NPC95585
0.8125	Intermediate Similarity	NPC282233
0.8118	Intermediate Similarity	NPC474955
0.8118	Intermediate Similarity	NPC327002
0.8118	Intermediate Similarity	NPC471898
0.8105	Intermediate Similarity	NPC310981
0.8095	Intermediate Similarity	NPC199595
0.809	Intermediate Similarity	NPC474474
0.8085	Intermediate Similarity	NPC471966
0.8085	Intermediate Similarity	NPC478056
0.8072	Intermediate Similarity	NPC471899
0.8072	Intermediate Similarity	NPC471897
0.8072	Intermediate Similarity	NPC107039
0.8068	Intermediate Similarity	NPC91525
0.8068	Intermediate Similarity	NPC9892
0.8068	Intermediate Similarity	NPC329943
0.8068	Intermediate Similarity	NPC10005
0.8068	Intermediate Similarity	NPC324063
0.8065	Intermediate Similarity	NPC58052
0.8065	Intermediate Similarity	NPC111684
0.8065	Intermediate Similarity	NPC471039
0.8046	Intermediate Similarity	NPC156981
0.8046	Intermediate Similarity	NPC96095
0.8043	Intermediate Similarity	NPC74751
0.8043	Intermediate Similarity	NPC471040
0.8043	Intermediate Similarity	NPC476415
0.8043	Intermediate Similarity	NPC294266
0.8025	Intermediate Similarity	NPC144947
0.8023	Intermediate Similarity	NPC15910
0.8023	Intermediate Similarity	NPC470813
0.8023	Intermediate Similarity	NPC100297
0.8023	Intermediate Similarity	NPC321289
0.8023	Intermediate Similarity	NPC327969
0.8022	Intermediate Similarity	NPC476187
0.8	Intermediate Similarity	NPC474700
0.8	Intermediate Similarity	NPC475049
0.8	Intermediate Similarity	NPC174342
0.8	Intermediate Similarity	NPC37038
0.7979	Intermediate Similarity	NPC204054
0.7979	Intermediate Similarity	NPC473456
0.7979	Intermediate Similarity	NPC257726
0.7978	Intermediate Similarity	NPC30421
0.7976	Intermediate Similarity	NPC115515
0.7976	Intermediate Similarity	NPC321514
0.7976	Intermediate Similarity	NPC74410
0.7955	Intermediate Similarity	NPC65661
0.7955	Intermediate Similarity	NPC76333
0.7955	Intermediate Similarity	NPC470223
0.7955	Intermediate Similarity	NPC474680
0.7952	Intermediate Similarity	NPC89294
0.7935	Intermediate Similarity	NPC295643
0.7935	Intermediate Similarity	NPC214756
0.7935	Intermediate Similarity	NPC263780
0.7935	Intermediate Similarity	NPC272075
0.7935	Intermediate Similarity	NPC79117
0.7931	Intermediate Similarity	NPC22611
0.7931	Intermediate Similarity	NPC271784
0.7912	Intermediate Similarity	NPC474842
0.7912	Intermediate Similarity	NPC475965
0.7912	Intermediate Similarity	NPC474728
0.7912	Intermediate Similarity	NPC120840
0.7912	Intermediate Similarity	NPC113989
0.7907	Intermediate Similarity	NPC40228
0.7907	Intermediate Similarity	NPC221647
0.7907	Intermediate Similarity	NPC229584
0.7907	Intermediate Similarity	NPC14203
0.7895	Intermediate Similarity	NPC194196
0.7889	Intermediate Similarity	NPC474845
0.7889	Intermediate Similarity	NPC226863
0.7889	Intermediate Similarity	NPC473229
0.7889	Intermediate Similarity	NPC472302
0.7889	Intermediate Similarity	NPC206060
0.7882	Intermediate Similarity	NPC471475
0.7882	Intermediate Similarity	NPC231431
0.7882	Intermediate Similarity	NPC16394
0.7882	Intermediate Similarity	NPC476177
0.7872	Intermediate Similarity	NPC122324
0.7872	Intermediate Similarity	NPC151725
0.7872	Intermediate Similarity	NPC106425
0.7865	Intermediate Similarity	NPC73038
0.7865	Intermediate Similarity	NPC264127
0.7865	Intermediate Similarity	NPC325594
0.7865	Intermediate Similarity	NPC220478
0.7857	Intermediate Similarity	NPC165711
0.7848	Intermediate Similarity	NPC4370
0.7848	Intermediate Similarity	NPC290350
0.7841	Intermediate Similarity	NPC320801
0.7841	Intermediate Similarity	NPC100391
0.7831	Intermediate Similarity	NPC279666
0.7831	Intermediate Similarity	NPC192540
0.7826	Intermediate Similarity	NPC60755
0.7826	Intermediate Similarity	NPC77099
0.7826	Intermediate Similarity	NPC233455
0.7826	Intermediate Similarity	NPC145067
0.7826	Intermediate Similarity	NPC285184
0.7826	Intermediate Similarity	NPC4036
0.7826	Intermediate Similarity	NPC65120
0.7826	Intermediate Similarity	NPC174167
0.7826	Intermediate Similarity	NPC470113
0.7826	Intermediate Similarity	NPC158030
0.7826	Intermediate Similarity	NPC470036
0.7826	Intermediate Similarity	NPC470590
0.7816	Intermediate Similarity	NPC240302
0.7816	Intermediate Similarity	NPC186276
0.7802	Intermediate Similarity	NPC5509
0.7802	Intermediate Similarity	NPC474570
0.7802	Intermediate Similarity	NPC168131
0.7802	Intermediate Similarity	NPC305039
0.7802	Intermediate Similarity	NPC50070
0.7802	Intermediate Similarity	NPC30522
0.7802	Intermediate Similarity	NPC284561
0.7791	Intermediate Similarity	NPC2482
0.7789	Intermediate Similarity	NPC476768
0.7789	Intermediate Similarity	NPC26413
0.7789	Intermediate Similarity	NPC226986
0.7789	Intermediate Similarity	NPC170131
0.7778	Intermediate Similarity	NPC470267
0.7778	Intermediate Similarity	NPC71507
0.7778	Intermediate Similarity	NPC158141
0.7778	Intermediate Similarity	NPC173089
0.7766	Intermediate Similarity	NPC33473
0.7766	Intermediate Similarity	NPC139459
0.7765	Intermediate Similarity	NPC198240
0.7753	Intermediate Similarity	NPC29447
0.7753	Intermediate Similarity	NPC86316
0.7753	Intermediate Similarity	NPC106416
0.7742	Intermediate Similarity	NPC169343
0.7742	Intermediate Similarity	NPC86368
0.7742	Intermediate Similarity	NPC298554
0.7738	Intermediate Similarity	NPC19907
0.7738	Intermediate Similarity	NPC180886
0.7738	Intermediate Similarity	NPC69143
0.7738	Intermediate Similarity	NPC41017
0.7738	Intermediate Similarity	NPC309399
0.7732	Intermediate Similarity	NPC63249
0.7727	Intermediate Similarity	NPC469561
0.7727	Intermediate Similarity	NPC97913
0.7727	Intermediate Similarity	NPC49019
0.7727	Intermediate Similarity	NPC105803
0.7717	Intermediate Similarity	NPC252737
0.7717	Intermediate Similarity	NPC469595
0.7717	Intermediate Similarity	NPC148414
0.7717	Intermediate Similarity	NPC175628
0.7717	Intermediate Similarity	NPC198818
0.7717	Intermediate Similarity	NPC471896
0.7717	Intermediate Similarity	NPC476369
0.7717	Intermediate Similarity	NPC476437
0.7717	Intermediate Similarity	NPC111585
0.7717	Intermediate Similarity	NPC212679
0.7717	Intermediate Similarity	NPC220454
0.7711	Intermediate Similarity	NPC103958

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 NPC2709 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	1729
0.2-0.3	4039
0.3-0.4	2160
0.4-0.5	602
0.5-0.6	216
0.6-0.7	162
0.7-0.8	36
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8295	Intermediate Similarity	NPD5737	Approved
0.8295	Intermediate Similarity	NPD6672	Approved
0.8295	Intermediate Similarity	NPD7513	Clinical (unspecified phase)
0.8276	Intermediate Similarity	NPD5330	Approved
0.8276	Intermediate Similarity	NPD7146	Approved
0.8276	Intermediate Similarity	NPD7521	Approved
0.8276	Intermediate Similarity	NPD7334	Approved
0.8276	Intermediate Similarity	NPD6684	Approved
0.8276	Intermediate Similarity	NPD6409	Approved
0.8242	Intermediate Similarity	NPD7901	Clinical (unspecified phase)
0.8242	Intermediate Similarity	NPD7900	Approved
0.8235	Intermediate Similarity	NPD4752	Clinical (unspecified phase)
0.809	Intermediate Similarity	NPD6903	Approved
0.8043	Intermediate Similarity	NPD7748	Approved
0.7979	Intermediate Similarity	NPD7902	Approved
0.7978	Intermediate Similarity	NPD3573	Approved
0.7826	Intermediate Similarity	NPD7515	Phase 2
0.7802	Intermediate Similarity	NPD6904	Approved
0.7802	Intermediate Similarity	NPD6080	Approved
0.7802	Intermediate Similarity	NPD6673	Approved
0.7742	Intermediate Similarity	NPD6399	Phase 3
0.7684	Intermediate Similarity	NPD7732	Phase 3
0.7634	Intermediate Similarity	NPD6050	Approved
0.7609	Intermediate Similarity	NPD7285	Clinical (unspecified phase)
0.7604	Intermediate Similarity	NPD6083	Phase 2
0.7604	Intermediate Similarity	NPD6084	Phase 2
0.7579	Intermediate Similarity	NPD5695	Phase 3
0.7579	Intermediate Similarity	NPD6356	Clinical (unspecified phase)
0.7527	Intermediate Similarity	NPD5692	Phase 3
0.75	Intermediate Similarity	NPD5208	Approved
0.7473	Intermediate Similarity	NPD6098	Approved
0.7447	Intermediate Similarity	NPD5693	Phase 1
0.7447	Intermediate Similarity	NPD5694	Approved
0.7386	Intermediate Similarity	NPD4695	Discontinued
0.7347	Intermediate Similarity	NPD5696	Approved
0.734	Intermediate Similarity	NPD5207	Approved
0.732	Intermediate Similarity	NPD7614	Phase 1
0.7253	Intermediate Similarity	NPD3133	Approved
0.7253	Intermediate Similarity	NPD3666	Approved
0.7253	Intermediate Similarity	NPD3665	Phase 1
0.7174	Intermediate Similarity	NPD1694	Approved
0.7143	Intermediate Similarity	NPD4691	Approved
0.7143	Intermediate Similarity	NPD4697	Phase 3
0.7115	Intermediate Similarity	NPD6899	Approved
0.7115	Intermediate Similarity	NPD6881	Approved
0.7113	Intermediate Similarity	NPD6001	Approved
0.7097	Intermediate Similarity	NPD3618	Phase 1
0.7087	Intermediate Similarity	NPD6402	Approved
0.7087	Intermediate Similarity	NPD5739	Approved
0.7087	Intermediate Similarity	NPD6675	Approved
0.7087	Intermediate Similarity	NPD7128	Approved
0.7083	Intermediate Similarity	NPD5284	Approved
0.7083	Intermediate Similarity	NPD6079	Approved
0.7083	Intermediate Similarity	NPD6411	Approved
0.7083	Intermediate Similarity	NPD5281	Approved
0.7083	Intermediate Similarity	NPD8035	Phase 2
0.7083	Intermediate Similarity	NPD8034	Phase 2
0.7075	Intermediate Similarity	NPD6650	Approved
0.7075	Intermediate Similarity	NPD6649	Approved
0.7065	Intermediate Similarity	NPD4786	Approved
0.7065	Intermediate Similarity	NPD3668	Phase 3
0.7053	Intermediate Similarity	NPD4753	Phase 2
0.7053	Intermediate Similarity	NPD5328	Approved
0.7048	Intermediate Similarity	NPD6372	Approved
0.7048	Intermediate Similarity	NPD6373	Approved
0.7041	Intermediate Similarity	NPD5654	Approved
0.7033	Intermediate Similarity	NPD4223	Phase 3
0.7033	Intermediate Similarity	NPD4221	Approved
0.7033	Intermediate Similarity	NPD3667	Approved
0.7024	Intermediate Similarity	NPD4137	Phase 3
0.7019	Intermediate Similarity	NPD5697	Approved
0.7011	Intermediate Similarity	NPD8039	Approved
0.7	Intermediate Similarity	NPD7638	Approved
0.6989	Remote Similarity	NPD5329	Approved
0.6981	Remote Similarity	NPD7290	Approved
0.6981	Remote Similarity	NPD6883	Approved
0.6981	Remote Similarity	NPD7102	Approved
0.6952	Remote Similarity	NPD7320	Approved
0.6952	Remote Similarity	NPD6011	Approved
0.6941	Remote Similarity	NPD4747	Approved
0.6931	Remote Similarity	NPD7640	Approved
0.6931	Remote Similarity	NPD7639	Approved
0.6923	Remote Similarity	NPD6008	Approved
0.6916	Remote Similarity	NPD6847	Approved
0.6916	Remote Similarity	NPD6617	Approved
0.6916	Remote Similarity	NPD6869	Approved
0.6916	Remote Similarity	NPD8130	Phase 1
0.6915	Remote Similarity	NPD5279	Phase 3
0.6915	Remote Similarity	NPD5690	Phase 2
0.6915	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5959	Approved
0.6897	Remote Similarity	NPD5733	Approved
0.6897	Remote Similarity	NPD4058	Approved
0.6893	Remote Similarity	NPD6052	Approved
0.6887	Remote Similarity	NPD6012	Approved
0.6887	Remote Similarity	NPD6014	Approved
0.6887	Remote Similarity	NPD6013	Approved
0.6882	Remote Similarity	NPD4197	Approved
0.6875	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6875	Remote Similarity	NPD6101	Approved
0.6875	Remote Similarity	NPD6051	Approved
0.6869	Remote Similarity	NPD5210	Approved
0.6869	Remote Similarity	NPD4629	Approved
0.6857	Remote Similarity	NPD6412	Phase 2
0.6857	Remote Similarity	NPD6614	Approved
0.6857	Remote Similarity	NPD5701	Approved
0.6852	Remote Similarity	NPD8297	Approved
0.6852	Remote Similarity	NPD6882	Approved
0.6809	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.68	Remote Similarity	NPD5222	Approved
0.68	Remote Similarity	NPD5221	Approved
0.6792	Remote Similarity	NPD6686	Approved
0.6778	Remote Similarity	NPD3617	Approved
0.6765	Remote Similarity	NPD6404	Discontinued
0.6759	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6757	Remote Similarity	NPD7115	Discovery
0.6739	Remote Similarity	NPD8028	Phase 2
0.6737	Remote Similarity	NPD4138	Approved
0.6737	Remote Similarity	NPD4693	Phase 3
0.6737	Remote Similarity	NPD4519	Discontinued
0.6737	Remote Similarity	NPD4689	Approved
0.6737	Remote Similarity	NPD5205	Approved
0.6737	Remote Similarity	NPD4623	Approved
0.6737	Remote Similarity	NPD4694	Approved
0.6737	Remote Similarity	NPD5280	Approved
0.6737	Remote Similarity	NPD4690	Approved
0.6737	Remote Similarity	NPD4688	Approved
0.6733	Remote Similarity	NPD5173	Approved
0.6705	Remote Similarity	NPD4687	Approved
0.6667	Remote Similarity	NPD4202	Approved
0.6667	Remote Similarity	NPD6868	Approved
0.6667	Remote Similarity	NPD5276	Approved
0.6636	Remote Similarity	NPD6858	Approved
0.6636	Remote Similarity	NPD7094	Approved
0.6602	Remote Similarity	NPD5286	Approved
0.6602	Remote Similarity	NPD4696	Approved
0.6602	Remote Similarity	NPD5285	Approved
0.6596	Remote Similarity	NPD4788	Approved
0.6574	Remote Similarity	NPD8132	Clinical (unspecified phase)
0.6569	Remote Similarity	NPD4755	Approved
0.6549	Remote Similarity	NPD6335	Approved
0.6542	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD5223	Approved
0.6522	Remote Similarity	NPD7645	Phase 2
0.6522	Remote Similarity	NPD4195	Approved
0.6518	Remote Similarity	NPD6274	Approved
0.6512	Remote Similarity	NPD3621	Clinical (unspecified phase)
0.6505	Remote Similarity	NPD4225	Approved
0.65	Remote Similarity	NPD5778	Approved
0.65	Remote Similarity	NPD5779	Approved
0.6491	Remote Similarity	NPD7101	Approved
0.6491	Remote Similarity	NPD7100	Approved
0.6486	Remote Similarity	NPD4632	Approved
0.6477	Remote Similarity	NPD5777	Approved
0.6476	Remote Similarity	NPD5225	Approved
0.6476	Remote Similarity	NPD4633	Approved
0.6476	Remote Similarity	NPD5211	Phase 2
0.6476	Remote Similarity	NPD5224	Approved
0.6476	Remote Similarity	NPD5226	Approved
0.6471	Remote Similarity	NPD5349	Clinical (unspecified phase)
0.646	Remote Similarity	NPD6317	Approved
0.6442	Remote Similarity	NPD4700	Approved
0.6415	Remote Similarity	NPD5175	Approved
0.6415	Remote Similarity	NPD5174	Approved
0.6404	Remote Similarity	NPD6313	Approved
0.6404	Remote Similarity	NPD6314	Approved
0.6364	Remote Similarity	NPD5955	Clinical (unspecified phase)
0.6355	Remote Similarity	NPD5141	Approved
0.6321	Remote Similarity	NPD7632	Discontinued
0.6316	Remote Similarity	NPD6009	Approved
0.6303	Remote Similarity	NPD7507	Approved
0.63	Remote Similarity	NPD4096	Approved
0.6293	Remote Similarity	NPD6319	Approved
0.6273	Remote Similarity	NPD4061	Clinical (unspecified phase)
0.6271	Remote Similarity	NPD8328	Phase 3
0.6271	Remote Similarity	NPD7604	Phase 2
0.6264	Remote Similarity	NPD6942	Approved
0.6264	Remote Similarity	NPD7339	Approved
0.6262	Remote Similarity	NPD4754	Approved
0.625	Remote Similarity	NPD3527	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD5983	Phase 2
0.6239	Remote Similarity	NPD6909	Approved
0.6239	Remote Similarity	NPD6908	Approved
0.6239	Remote Similarity	NPD6291	Clinical (unspecified phase)
0.6218	Remote Similarity	NPD7492	Approved
0.6211	Remote Similarity	NPD4139	Approved
0.6211	Remote Similarity	NPD4692	Approved
0.6198	Remote Similarity	NPD7736	Approved
0.6196	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6182	Remote Similarity	NPD5128	Approved
0.6182	Remote Similarity	NPD4729	Approved
0.6182	Remote Similarity	NPD5168	Approved
0.6182	Remote Similarity	NPD4730	Approved
0.6176	Remote Similarity	NPD5133	Approved
0.6168	Remote Similarity	NPD5091	Approved
0.6167	Remote Similarity	NPD6336	Discontinued
0.6167	Remote Similarity	NPD6616	Approved
0.6154	Remote Similarity	NPD6054	Approved
0.6148	Remote Similarity	NPD7319	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