NPASS Compound

Structure

NPC472473 OpenBabel07101718292D 25 27 0 0 1 0 0 0 0 0999 V2000 -2.5385 0.0563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2327 0.4164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2601 1.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4680 -3.2382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8564 -2.5180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9975 -1.0707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 1.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3090 0.9511 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6974 -1.2308 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 -1.5909 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -2.5388 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4895 -0.2527 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3090 0.9511 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2601 -2.2601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1132 -3.1871 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9543 -1.9000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.3090 -1.9511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3090 -1.9511 0.0000 C 0 0 2 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 0.0000 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3212 -4.1653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2601 -2.2601 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1622 -2.8781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 12 1 0 0 0 0 2 12 1 0 0 0 0 4 14 2 0 0 0 0 5 15 1 0 0 0 0 6 22 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 18 1 0 0 0 0 9 12 2 0 0 0 0 9 16 1 0 0 0 0 10 14 1 0 0 0 0 10 16 1 0 0 0 0 11 17 1 0 0 0 0 11 19 1 0 0 0 0 13 3 1 6 0 0 0 13 20 1 0 0 0 0 15 23 2 0 0 0 0 15 25 1 0 0 0 0 16 25 1 0 0 0 0 17 14 1 1 0 0 0 17 21 1 0 0 0 0 18 20 1 0 0 0 0 18 22 1 6 0 0 0 19 22 1 6 0 0 0 19 24 1 0 0 0 0 20 21 1 0 0 0 0 21 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	346.25
Volume:	381.86
LogP:	3.982
LogD:	4.198
LogS:	-3.847
# Rotatable Bonds:	6
TPSA:	46.53
# H-Bond Aceptor:	3
# H-Bond Donor:	1
# Rings:	3
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.588
Synthetic Accessibility Score:	5.023
Fsp3:	0.773
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.589
MDCK Permeability:	7.234911026898772e-05
Pgp-inhibitor:	0.12
Pgp-substrate:	0.179
Human Intestinal Absorption (HIA):	0.012
20% Bioavailability (F20%):	0.033
30% Bioavailability (F30%):	0.033

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.145
Plasma Protein Binding (PPB):	87.50452423095703%
Volume Distribution (VD):	1.571
Pgp-substrate:	8.907327651977539%

ADMET: Metabolism

CYP1A2-inhibitor:	0.214
CYP1A2-substrate:	0.101
CYP2C19-inhibitor:	0.031
CYP2C19-substrate:	0.87
CYP2C9-inhibitor:	0.074
CYP2C9-substrate:	0.133
CYP2D6-inhibitor:	0.006
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.245
CYP3A4-substrate:	0.515

ADMET: Excretion

Clearance (CL):	7.869
Half-life (T1/2):	0.524

ADMET: Toxicity

hERG Blockers:	0.194
Human Hepatotoxicity (H-HT):	0.869
Drug-inuced Liver Injury (DILI):	0.803
AMES Toxicity:	0.054
Rat Oral Acute Toxicity:	0.081
Maximum Recommended Daily Dose:	0.103
Skin Sensitization:	0.083
Carcinogencity:	0.007
Eye Corrosion:	0.005
Eye Irritation:	0.066
Respiratory Toxicity:	0.657

Download Data

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

Natural Product: NPC472473

Natural Product ID:	NPC472473
*Common Name:**	LUPDHBLMFRBDDB-GAQFUSPISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	LUPDHBLMFRBDDB-GAQFUSPISA-N
Standard InCHI:	InChI=1S/C22H34O3/c1-12(2)9-16(25-15(5)23)10-14(4)17-11-19(24)22(6)18-8-7-13(3)20(18)21(17)22/h9,13,16-21,24H,4,7-8,10-11H2,1-3,5-6H3/t13-,16?,17+,18+,19-,20-,21+,22+/m1/s1
SMILES:	CC(=O)OC(CC(=C)[C@@H]1C[C@H]([C@]2([C@@H]1[C@@H]1[C@H](C)CC[C@H]21)C)O)C=C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3425795
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids [CHEMONTID:0001595] Spatane and 4,10-secospatane 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
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	Eukaryota	n.a.	At a depth of 510 m, Gulf of Mannar near Mandapam coast (9 16'N, 79 12'E), Tamilnadu, India	2013-May	PMID[25978960]
NPO5780	Stoechospermum marginatum	Species	Dictyotaceae	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	5
MIC	4
Others	4

Activity Type	# Activity
Cell Line	2
NON-MOLECULAR	3
Organism	8

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT407	Cell Line	COLO 205	Homo sapiens	IC50	=	87.34	ug.mL-1	PMID[448211]
NPT1970	Cell Line	THP-1	Homo sapiens	IC50	=	50.28	ug.mL-1	PMID[448211]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	=	200.0	ug.mL-1	PMID[448211]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	IZ	=	11.67	mm	PMID[448211]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IZ	=	10.33	mm	PMID[448211]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	IZ	=	0.0	mm	PMID[448211]
NPT19	Organism	Escherichia coli	Escherichia coli	IZ	=	10.67	mm	PMID[448211]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	198.34	ug.mL-1	PMID[448211]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	73.22	ug.mL-1	PMID[448211]
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	=	60.02	ug.mL-1	PMID[448211]
NPT173	Organism	Klebsiella pneumoniae	Klebsiella pneumoniae	MIC	=	200.0	ug.mL-1	PMID[448211]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	MIC	=	200.0	ug.mL-1	PMID[448211]
NPT79	Organism	Bacillus subtilis	Bacillus subtilis	MIC	=	400.0	ug.mL-1	PMID[448211]

☑ 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 NPC472473 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	186
0.1-0.2	1430
0.2-0.3	7627
0.3-0.4	15582
0.4-0.5	8143
0.5-0.6	6909
0.6-0.7	2617
0.7-0.8	191
0.8-0.85	5
0.85-0.9	4
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9359	High Similarity	NPC472470
0.9	High Similarity	NPC472471
0.8851	High Similarity	NPC472467
0.8846	High Similarity	NPC472472
0.8721	High Similarity	NPC472466
0.8621	High Similarity	NPC472468
0.8375	Intermediate Similarity	NPC476317
0.8375	Intermediate Similarity	NPC310643
0.8312	Intermediate Similarity	NPC22301
0.8272	Intermediate Similarity	NPC476439
0.825	Intermediate Similarity	NPC113639
0.8161	Intermediate Similarity	NPC45957
0.8161	Intermediate Similarity	NPC471657
0.8118	Intermediate Similarity	NPC477667
0.8077	Intermediate Similarity	NPC101622
0.8046	Intermediate Similarity	NPC477668
0.8	Intermediate Similarity	NPC472465
0.7978	Intermediate Similarity	NPC473647
0.7976	Intermediate Similarity	NPC80622
0.7975	Intermediate Similarity	NPC4299
0.7935	Intermediate Similarity	NPC472469
0.7875	Intermediate Similarity	NPC472254
0.7802	Intermediate Similarity	NPC234335
0.7792	Intermediate Similarity	NPC238352
0.7792	Intermediate Similarity	NPC477009
0.7778	Intermediate Similarity	NPC234527
0.7778	Intermediate Similarity	NPC14352
0.7753	Intermediate Similarity	NPC474832
0.7722	Intermediate Similarity	NPC224532
0.7701	Intermediate Similarity	NPC23748
0.7683	Intermediate Similarity	NPC474524
0.7683	Intermediate Similarity	NPC475517
0.7647	Intermediate Similarity	NPC325869
0.7647	Intermediate Similarity	NPC242767
0.764	Intermediate Similarity	NPC137253
0.7619	Intermediate Similarity	NPC186109
0.7595	Intermediate Similarity	NPC477791
0.759	Intermediate Similarity	NPC313185
0.7579	Intermediate Similarity	NPC477949
0.7579	Intermediate Similarity	NPC231751
0.7561	Intermediate Similarity	NPC477085
0.7553	Intermediate Similarity	NPC476488
0.7553	Intermediate Similarity	NPC476487
0.7529	Intermediate Similarity	NPC470944
0.7528	Intermediate Similarity	NPC475860
0.7528	Intermediate Similarity	NPC473659
0.7528	Intermediate Similarity	NPC471795
0.7528	Intermediate Similarity	NPC474694
0.7527	Intermediate Similarity	NPC472954
0.7527	Intermediate Similarity	NPC37816
0.7526	Intermediate Similarity	NPC222875
0.7526	Intermediate Similarity	NPC295110
0.7526	Intermediate Similarity	NPC25177
0.7526	Intermediate Similarity	NPC268829
0.7526	Intermediate Similarity	NPC247701
0.75	Intermediate Similarity	NPC301969
0.75	Intermediate Similarity	NPC472377
0.75	Intermediate Similarity	NPC37607
0.75	Intermediate Similarity	NPC49208
0.75	Intermediate Similarity	NPC311070
0.75	Intermediate Similarity	NPC471340
0.75	Intermediate Similarity	NPC474809
0.7473	Intermediate Similarity	NPC471952
0.7471	Intermediate Similarity	NPC471661
0.7471	Intermediate Similarity	NPC475944
0.7471	Intermediate Similarity	NPC474731
0.7471	Intermediate Similarity	NPC82986
0.7471	Intermediate Similarity	NPC474683
0.7471	Intermediate Similarity	NPC474759
0.7471	Intermediate Similarity	NPC474752
0.7471	Intermediate Similarity	NPC7505
0.747	Intermediate Similarity	NPC309178
0.747	Intermediate Similarity	NPC471659
0.7447	Intermediate Similarity	NPC90453
0.7444	Intermediate Similarity	NPC329692
0.7444	Intermediate Similarity	NPC286153
0.7444	Intermediate Similarity	NPC474970
0.7442	Intermediate Similarity	NPC226226
0.7442	Intermediate Similarity	NPC55304
0.7439	Intermediate Similarity	NPC477086
0.7439	Intermediate Similarity	NPC477087
0.7439	Intermediate Similarity	NPC471662
0.7436	Intermediate Similarity	NPC309300
0.7423	Intermediate Similarity	NPC290802
0.7419	Intermediate Similarity	NPC177641
0.7419	Intermediate Similarity	NPC290651
0.7419	Intermediate Similarity	NPC221282
0.7416	Intermediate Similarity	NPC474693
0.7412	Intermediate Similarity	NPC84360
0.7412	Intermediate Similarity	NPC262747
0.74	Intermediate Similarity	NPC220217
0.74	Intermediate Similarity	NPC119855
0.7396	Intermediate Similarity	NPC69385
0.7396	Intermediate Similarity	NPC161493
0.7396	Intermediate Similarity	NPC475894
0.7391	Intermediate Similarity	NPC477215
0.7391	Intermediate Similarity	NPC476388
0.7391	Intermediate Similarity	NPC232747
0.7375	Intermediate Similarity	NPC472266
0.7374	Intermediate Similarity	NPC97487
0.7374	Intermediate Similarity	NPC474775
0.7374	Intermediate Similarity	NPC160583
0.7374	Intermediate Similarity	NPC187302
0.7374	Intermediate Similarity	NPC183570
0.7374	Intermediate Similarity	NPC189588
0.7374	Intermediate Similarity	NPC196471
0.7374	Intermediate Similarity	NPC10232
0.7368	Intermediate Similarity	NPC52044
0.7368	Intermediate Similarity	NPC67584
0.7368	Intermediate Similarity	NPC20546
0.7363	Intermediate Similarity	NPC312561
0.7349	Intermediate Similarity	NPC329763
0.7347	Intermediate Similarity	NPC477950
0.7342	Intermediate Similarity	NPC19569
0.7333	Intermediate Similarity	NPC245434
0.7326	Intermediate Similarity	NPC260814
0.7326	Intermediate Similarity	NPC27949
0.7326	Intermediate Similarity	NPC474816
0.7326	Intermediate Similarity	NPC323249
0.7326	Intermediate Similarity	NPC39547
0.7326	Intermediate Similarity	NPC474005
0.7326	Intermediate Similarity	NPC209135
0.732	Intermediate Similarity	NPC181147
0.732	Intermediate Similarity	NPC222011
0.732	Intermediate Similarity	NPC471610
0.7317	Intermediate Similarity	NPC469660
0.7317	Intermediate Similarity	NPC254845
0.7312	Intermediate Similarity	NPC78973
0.7303	Intermediate Similarity	NPC42476
0.7303	Intermediate Similarity	NPC321385
0.7303	Intermediate Similarity	NPC30502
0.73	Intermediate Similarity	NPC473577
0.73	Intermediate Similarity	NPC475585
0.73	Intermediate Similarity	NPC474550
0.7294	Intermediate Similarity	NPC469880
0.7294	Intermediate Similarity	NPC477202
0.7292	Intermediate Similarity	NPC88009
0.7292	Intermediate Similarity	NPC213078
0.7292	Intermediate Similarity	NPC18019
0.7292	Intermediate Similarity	NPC24956
0.7284	Intermediate Similarity	NPC167527
0.7283	Intermediate Similarity	NPC473879
0.7283	Intermediate Similarity	NPC472378
0.7283	Intermediate Similarity	NPC294480
0.7273	Intermediate Similarity	NPC474894
0.7273	Intermediate Similarity	NPC88735
0.7273	Intermediate Similarity	NPC316844
0.7273	Intermediate Similarity	NPC59994
0.7273	Intermediate Similarity	NPC78677
0.7273	Intermediate Similarity	NPC112868
0.7263	Intermediate Similarity	NPC281775
0.7263	Intermediate Similarity	NPC201725
0.7263	Intermediate Similarity	NPC474922
0.7263	Intermediate Similarity	NPC53685
0.7253	Intermediate Similarity	NPC56593
0.7253	Intermediate Similarity	NPC131813
0.725	Intermediate Similarity	NPC162309
0.7245	Intermediate Similarity	NPC473510
0.7245	Intermediate Similarity	NPC201406
0.7245	Intermediate Similarity	NPC227865
0.7245	Intermediate Similarity	NPC472826
0.7241	Intermediate Similarity	NPC469690
0.7241	Intermediate Similarity	NPC100906
0.7241	Intermediate Similarity	NPC44083
0.7241	Intermediate Similarity	NPC89128
0.7241	Intermediate Similarity	NPC86971
0.7241	Intermediate Similarity	NPC153987
0.7241	Intermediate Similarity	NPC477088
0.7234	Intermediate Similarity	NPC2882
0.7234	Intermediate Similarity	NPC249034
0.7234	Intermediate Similarity	NPC219874
0.7228	Intermediate Similarity	NPC186668
0.7228	Intermediate Similarity	NPC475290
0.7222	Intermediate Similarity	NPC37005
0.7222	Intermediate Similarity	NPC165064
0.7222	Intermediate Similarity	NPC96055
0.7222	Intermediate Similarity	NPC82297
0.7222	Intermediate Similarity	NPC16887
0.7222	Intermediate Similarity	NPC154893
0.7222	Intermediate Similarity	NPC53011
0.7222	Intermediate Similarity	NPC156485
0.7216	Intermediate Similarity	NPC210337
0.7216	Intermediate Similarity	NPC202705
0.7209	Intermediate Similarity	NPC283619
0.7209	Intermediate Similarity	NPC477203
0.7209	Intermediate Similarity	NPC471454
0.7209	Intermediate Similarity	NPC40049
0.7204	Intermediate Similarity	NPC177141
0.7204	Intermediate Similarity	NPC212664
0.7204	Intermediate Similarity	NPC474396
0.7204	Intermediate Similarity	NPC146554
0.7204	Intermediate Similarity	NPC50488
0.72	Intermediate Similarity	NPC36688
0.72	Intermediate Similarity	NPC476237
0.72	Intermediate Similarity	NPC472821
0.72	Intermediate Similarity	NPC280566
0.7191	Intermediate Similarity	NPC471298
0.7191	Intermediate Similarity	NPC7414
0.7191	Intermediate Similarity	NPC470049
0.7191	Intermediate Similarity	NPC89555

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 NPC472473 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	184
0.1-0.2	1974
0.2-0.3	4207
0.3-0.4	2010
0.4-0.5	436
0.5-0.6	262
0.6-0.7	67
0.7-0.8	9
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
0.8353	Intermediate Similarity	NPD6082	Clinical (unspecified phase)
0.7907	Intermediate Similarity	NPD5332	Approved
0.7907	Intermediate Similarity	NPD5362	Discontinued
0.7907	Intermediate Similarity	NPD5331	Approved
0.7882	Intermediate Similarity	NPD4790	Discontinued
0.7558	Intermediate Similarity	NPD5790	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD5785	Approved
0.7391	Intermediate Similarity	NPD6051	Approved
0.7356	Intermediate Similarity	NPD4820	Approved
0.7356	Intermediate Similarity	NPD4819	Approved
0.7356	Intermediate Similarity	NPD4822	Approved
0.7356	Intermediate Similarity	NPD4821	Approved
0.7326	Intermediate Similarity	NPD5784	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4268	Approved
0.7326	Intermediate Similarity	NPD4271	Approved
0.7191	Intermediate Similarity	NPD4269	Approved
0.7191	Intermediate Similarity	NPD4270	Approved
0.7174	Intermediate Similarity	NPD4251	Approved
0.7174	Intermediate Similarity	NPD4250	Approved
0.7143	Intermediate Similarity	NPD7638	Approved
0.7111	Intermediate Similarity	NPD7154	Phase 3
0.7079	Intermediate Similarity	NPD5369	Approved
0.7071	Intermediate Similarity	NPD7640	Approved
0.7071	Intermediate Similarity	NPD7639	Approved
0.7065	Intermediate Similarity	NPD5786	Approved
0.7065	Intermediate Similarity	NPD4249	Approved
0.7059	Intermediate Similarity	NPD6924	Approved
0.7059	Intermediate Similarity	NPD6926	Approved
0.7053	Intermediate Similarity	NPD7637	Suspended
0.7	Intermediate Similarity	NPD6435	Approved
0.6966	Remote Similarity	NPD4252	Approved
0.6957	Remote Similarity	NPD5363	Approved
0.6923	Remote Similarity	NPD6695	Phase 3
0.6915	Remote Similarity	NPD6903	Approved
0.6897	Remote Similarity	NPD3701	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD6933	Approved
0.6854	Remote Similarity	NPD6929	Approved
0.6848	Remote Similarity	NPD5766	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6848	Remote Similarity	NPD6400	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD6053	Discontinued
0.6804	Remote Similarity	NPD6399	Phase 3
0.6786	Remote Similarity	NPD6923	Approved
0.6786	Remote Similarity	NPD6922	Approved
0.6782	Remote Similarity	NPD7339	Approved
0.6782	Remote Similarity	NPD6942	Approved
0.6778	Remote Similarity	NPD6930	Phase 2
0.6778	Remote Similarity	NPD6931	Approved
0.6778	Remote Similarity	NPD5368	Approved
0.6768	Remote Similarity	NPD4792	Clinical (unspecified phase)
0.6707	Remote Similarity	NPD2685	Clinical (unspecified phase)
0.6706	Remote Similarity	NPD7143	Approved
0.6706	Remote Similarity	NPD7144	Approved
0.6702	Remote Similarity	NPD7521	Approved
0.6702	Remote Similarity	NPD7334	Approved
0.6702	Remote Similarity	NPD6684	Approved
0.6702	Remote Similarity	NPD6409	Approved
0.6702	Remote Similarity	NPD7146	Approved
0.6702	Remote Similarity	NPD5330	Approved
0.67	Remote Similarity	NPD6083	Phase 2
0.67	Remote Similarity	NPD6084	Phase 2
0.6667	Remote Similarity	NPD4786	Approved
0.6667	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6371	Approved
0.6634	Remote Similarity	NPD4225	Approved
0.6632	Remote Similarity	NPD7524	Approved
0.6632	Remote Similarity	NPD4751	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD7750	Discontinued
0.6629	Remote Similarity	NPD6925	Approved
0.6629	Remote Similarity	NPD5776	Phase 2
0.6628	Remote Similarity	NPD7151	Approved
0.6628	Remote Similarity	NPD7152	Approved
0.6628	Remote Similarity	NPD7150	Approved
0.6604	Remote Similarity	NPD7320	Approved
0.6598	Remote Similarity	NPD7838	Discovery
0.6593	Remote Similarity	NPD7514	Phase 3
0.6562	Remote Similarity	NPD7513	Clinical (unspecified phase)
0.6556	Remote Similarity	NPD7145	Approved
0.6556	Remote Similarity	NPD7322	Clinical (unspecified phase)
0.6522	Remote Similarity	NPD6902	Approved
0.6518	Remote Similarity	NPD7328	Approved
0.6518	Remote Similarity	NPD7327	Approved
0.6509	Remote Similarity	NPD7899	Clinical (unspecified phase)
0.65	Remote Similarity	NPD5695	Phase 3
0.6495	Remote Similarity	NPD1695	Approved
0.6491	Remote Similarity	NPD8033	Approved
0.6489	Remote Similarity	NPD3665	Phase 1
0.6489	Remote Similarity	NPD3666	Approved
0.6489	Remote Similarity	NPD3133	Approved
0.6477	Remote Similarity	NPD4784	Approved
0.6477	Remote Similarity	NPD4785	Approved
0.646	Remote Similarity	NPD7516	Approved
0.6452	Remote Similarity	NPD5209	Approved
0.6452	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD3667	Approved
0.6444	Remote Similarity	NPD6932	Approved
0.6442	Remote Similarity	NPD7632	Discontinued
0.6437	Remote Similarity	NPD4243	Approved
0.6429	Remote Similarity	NPD6698	Approved
0.6429	Remote Similarity	NPD46	Approved
0.6421	Remote Similarity	NPD6893	Approved
0.6415	Remote Similarity	NPD5739	Approved
0.6415	Remote Similarity	NPD6402	Approved
0.6415	Remote Similarity	NPD6675	Approved
0.6415	Remote Similarity	NPD7128	Approved
0.6413	Remote Similarity	NPD7332	Phase 2
0.6413	Remote Similarity	NPD7525	Registered
0.6413	Remote Similarity	NPD7509	Discontinued
0.6404	Remote Similarity	NPD8294	Approved
0.6404	Remote Similarity	NPD8377	Approved
0.6404	Remote Similarity	NPD8039	Approved
0.6386	Remote Similarity	NPD5325	Clinical (unspecified phase)
0.6364	Remote Similarity	NPD6411	Approved
0.6364	Remote Similarity	NPD7087	Discontinued
0.6364	Remote Similarity	NPD5693	Phase 1
0.6354	Remote Similarity	NPD6098	Approved
0.6348	Remote Similarity	NPD8380	Approved
0.6348	Remote Similarity	NPD8296	Approved
0.6348	Remote Similarity	NPD8335	Approved
0.6348	Remote Similarity	NPD8379	Approved
0.6348	Remote Similarity	NPD8378	Approved
0.6311	Remote Similarity	NPD5696	Approved
0.6304	Remote Similarity	NPD4195	Approved
0.6304	Remote Similarity	NPD6683	Phase 2
0.63	Remote Similarity	NPD5778	Approved
0.63	Remote Similarity	NPD5779	Approved
0.6296	Remote Similarity	NPD6899	Approved
0.6296	Remote Similarity	NPD6881	Approved
0.6283	Remote Similarity	NPD7115	Discovery
0.625	Remote Similarity	NPD7520	Clinical (unspecified phase)
0.625	Remote Similarity	NPD1694	Approved
0.6239	Remote Similarity	NPD6373	Approved
0.6239	Remote Similarity	NPD6372	Approved
0.6237	Remote Similarity	NPD4748	Discontinued
0.6224	Remote Similarity	NPD5737	Approved
0.6224	Remote Similarity	NPD6672	Approved
0.6222	Remote Similarity	NPD8264	Approved
0.6207	Remote Similarity	NPD7503	Approved
0.6204	Remote Similarity	NPD5697	Approved
0.6204	Remote Similarity	NPD5701	Approved
0.619	Remote Similarity	NPD5344	Discontinued
0.6186	Remote Similarity	NPD5279	Phase 3
0.6182	Remote Similarity	NPD7290	Approved
0.6182	Remote Similarity	NPD6883	Approved
0.6182	Remote Similarity	NPD7102	Approved
0.6176	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.617	Remote Similarity	NPD6898	Phase 1
0.6162	Remote Similarity	NPD6080	Approved
0.6162	Remote Similarity	NPD5328	Approved
0.6162	Remote Similarity	NPD5370	Suspended
0.6162	Remote Similarity	NPD6904	Approved
0.6162	Remote Similarity	NPD4753	Phase 2
0.6162	Remote Similarity	NPD6101	Approved
0.6162	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6162	Remote Similarity	NPD6673	Approved
0.6147	Remote Similarity	NPD6686	Approved
0.6147	Remote Similarity	NPD6011	Approved
0.6139	Remote Similarity	NPD4202	Approved
0.6134	Remote Similarity	NPD7507	Approved
0.6126	Remote Similarity	NPD6847	Approved
0.6126	Remote Similarity	NPD6649	Approved
0.6126	Remote Similarity	NPD6869	Approved
0.6126	Remote Similarity	NPD8130	Phase 1
0.6126	Remote Similarity	NPD6617	Approved
0.6126	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6126	Remote Similarity	NPD6650	Approved
0.6105	Remote Similarity	NPD4221	Approved
0.6105	Remote Similarity	NPD4223	Phase 3
0.61	Remote Similarity	NPD5207	Approved
0.6098	Remote Similarity	NPD3198	Approved
0.6091	Remote Similarity	NPD6012	Approved
0.6091	Remote Similarity	NPD6013	Approved
0.6091	Remote Similarity	NPD6014	Approved
0.6082	Remote Similarity	NPD5329	Approved
0.6071	Remote Similarity	NPD8297	Approved
0.6071	Remote Similarity	NPD6882	Approved
0.6061	Remote Similarity	NPD5208	Approved
0.6044	Remote Similarity	NPD4190	Phase 3
0.6044	Remote Similarity	NPD5275	Approved
0.6042	Remote Similarity	NPD4788	Approved
0.604	Remote Similarity	NPD6079	Approved
0.604	Remote Similarity	NPD5284	Approved
0.604	Remote Similarity	NPD4810	Clinical (unspecified phase)
0.604	Remote Similarity	NPD5281	Approved
0.604	Remote Similarity	NPD8035	Phase 2
0.604	Remote Similarity	NPD6050	Approved
0.604	Remote Similarity	NPD7983	Approved
0.604	Remote Similarity	NPD8034	Phase 2
0.6036	Remote Similarity	NPD6420	Discontinued
0.602	Remote Similarity	NPD3618	Phase 1
0.6	Remote Similarity	NPD8029	Clinical (unspecified phase)
0.6	Remote Similarity	NPD857	Phase 3
0.5984	Remote Similarity	NPD7319	Approved
0.5979	Remote Similarity	NPD4197	Approved
0.5963	Remote Similarity	NPD6008	Approved
0.5957	Remote Similarity	NPD7645	Phase 2
0.5952	Remote Similarity	NPD368	Approved
0.5943	Remote Similarity	NPD6648	Approved
0.5941	Remote Similarity	NPD5692	Phase 3
0.5922	Remote Similarity	NPD5707	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