NPASS Compound

Structure

CID151939 OpenBabel06191715522D 25 28 0 0 1 0 0 0 0 0999 V2000 -0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7355 -3.4914 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0700 -2.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5240 -2.8965 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0714 -1.9532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9794 -3.7352 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 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 -1.8320 -2.2412 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3826 -3.9360 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5391 -2.9483 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5267 -2.7919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 2 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 -3.9807 -3.6829 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.2736 -4.3900 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 15 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 5 6 2 0 0 0 0 5 7 1 0 0 0 0 6 8 1 0 0 0 0 7 17 2 0 0 0 0 8 20 2 0 0 0 0 9 10 1 0 0 0 0 9 15 1 0 0 0 0 11 12 1 0 0 0 0 11 19 2 0 0 0 0 12 21 1 0 0 0 0 13 16 1 0 0 0 0 13 23 1 0 0 0 0 14 16 2 0 0 0 0 14 24 1 0 0 0 0 15 23 1 1 0 0 0 16 17 1 0 0 0 0 17 20 1 0 0 0 0 18 10 1 6 0 0 0 18 19 1 0 0 0 0 18 22 1 0 0 0 0 19 23 1 0 0 0 0 20 24 1 0 0 0 0 21 22 1 0 0 0 0 21 25 1 6 0 0 0 23 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	337.24
Volume:	378.743
LogP:	5.74
LogD:	4.617
LogS:	-5.576
# Rotatable Bonds:	2
TPSA:	36.02
# H-Bond Aceptor:	2
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	2

MedChem Properties

QED Drug-Likeness Score:	0.699
Synthetic Accessibility Score:	4.071
Fsp3:	0.565
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.625
MDCK Permeability:	1.6635302017675713e-05
Pgp-inhibitor:	0.987
Pgp-substrate:	0.019
Human Intestinal Absorption (HIA):	0.003
20% Bioavailability (F20%):	0.98
30% Bioavailability (F30%):	0.988

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.163
Plasma Protein Binding (PPB):	98.55569458007812%
Volume Distribution (VD):	1.44
Pgp-substrate:	2.6467056274414062%

ADMET: Metabolism

CYP1A2-inhibitor:	0.294
CYP1A2-substrate:	0.587
CYP2C19-inhibitor:	0.718
CYP2C19-substrate:	0.599
CYP2C9-inhibitor:	0.756
CYP2C9-substrate:	0.949
CYP2D6-inhibitor:	0.804
CYP2D6-substrate:	0.893
CYP3A4-inhibitor:	0.828
CYP3A4-substrate:	0.458

ADMET: Excretion

Clearance (CL):	7.057
Half-life (T1/2):	0.151

ADMET: Toxicity

hERG Blockers:	0.058
Human Hepatotoxicity (H-HT):	0.164
Drug-inuced Liver Injury (DILI):	0.041
AMES Toxicity:	0.006
Rat Oral Acute Toxicity:	0.849
Maximum Recommended Daily Dose:	0.991
Skin Sensitization:	0.523
Carcinogencity:	0.042
Eye Corrosion:	0.009
Eye Irritation:	0.353
Respiratory Toxicity:	0.963

Download Data

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

Natural Product: NPC151939

Natural Product ID:	NPC151939
*Common Name:**	Polyalthenol
IUPAC Name:	(2S,5R,6R,8aR)-5-(1H-indol-3-ylmethyl)-1,1,5,6-tetramethyl-2,3,6,7,8,8a-hexahydronaphthalen-2-ol
Synonyms:	Polyalthenol
Standard InCHIKey:	KKNODFPXRCYCJH-LJTXAQECSA-N
Standard InCHI:	InChI=1S/C23H31NO/c1-15-9-10-18-19(11-12-21(25)22(18,2)3)23(15,4)13-16-14-24-20-8-6-5-7-17(16)20/h5-8,11,14-15,18,21,24-25H,9-10,12-13H2,1-4H3/t15-,18-,21+,23-/m1/s1
SMILES:	C[C@@H]1CC[C@@H]2C(=CC[C@@H](C2(C)C)O)[C@]1(C)Cc1c[nH]c2c1cccc2
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1095763
PubChem CID:	21602731
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000002] Organoheterocyclic compounds [CHEMONTID:0000211] Indoles and derivatives [CHEMONTID:0002497] Indoles [CHEMONTID:0004196] 3-alkylindoles

*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
NPO22519	Greenwayodendron suaveolens	Species	Annonaceae	Eukaryota	n.a.	fruit	n.a.	PMID[15679334]
NPO10599	Epichloe typhina	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17587677]
NPO22519	Greenwayodendron suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20405845]
NPO10599	Epichloe typhina	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[447932]
NPO8594	Eupatorium glaucescens	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5317	Diatenopteryx sorbifolia	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1696	Sedum lydium	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5797	Chrysosporium lobatum	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2121	Ranunculus glaber	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1095	Cirrhopetalum elatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO94	Teucrium cubense	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10599	Epichloe typhina	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22519	Greenwayodendron suaveolens	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8594	Eupatorium glaucescens	Species	Asteraceae	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
MIC	13
Others	1

Activity Type	# Activity
Organism	14

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	1.0	ug.mL-1	PMID[465853]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	2.0	ug.mL-1	PMID[465853]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	=	4.0	ug.mL-1	PMID[465853]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC90	=	4.0	ug.mL-1	PMID[465853]

☑ 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 NPC151939 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	352
0.1-0.2	1708
0.2-0.3	9330
0.3-0.4	22495
0.4-0.5	4520
0.5-0.6	1880
0.6-0.7	1588
0.7-0.8	709
0.8-0.85	89
0.85-0.9	22
0.9-0.95	2
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.963	High Similarity	NPC300688
0.9497	High Similarity	NPC201700
0.9018	High Similarity	NPC154293
0.8953	High Similarity	NPC95783
0.8951	High Similarity	NPC311276
0.8875	High Similarity	NPC469785
0.8834	High Similarity	NPC40779
0.882	High Similarity	NPC469762
0.8757	High Similarity	NPC213468
0.875	High Similarity	NPC469763
0.875	High Similarity	NPC73952
0.875	High Similarity	NPC25008
0.875	High Similarity	NPC469786
0.875	High Similarity	NPC259644
0.875	High Similarity	NPC469765
0.875	High Similarity	NPC469760
0.8696	High Similarity	NPC70922
0.8696	High Similarity	NPC80597
0.8696	High Similarity	NPC212376
0.8696	High Similarity	NPC75540
0.8696	High Similarity	NPC211572
0.869	High Similarity	NPC275305
0.869	High Similarity	NPC37423
0.865	High Similarity	NPC230869
0.8631	High Similarity	NPC97525
0.8614	High Similarity	NPC49954
0.8614	High Similarity	NPC474561
0.8605	High Similarity	NPC19679
0.8589	High Similarity	NPC286427
0.8588	High Similarity	NPC68354
0.8563	High Similarity	NPC63751
0.8538	High Similarity	NPC215795
0.8538	High Similarity	NPC176199
0.8521	High Similarity	NPC313791
0.8512	High Similarity	NPC194411
0.8503	High Similarity	NPC54988
0.8503	High Similarity	NPC160105
0.8494	Intermediate Similarity	NPC102423
0.8491	Intermediate Similarity	NPC314372
0.8462	Intermediate Similarity	NPC300183
0.8434	Intermediate Similarity	NPC282231
0.8424	Intermediate Similarity	NPC41257
0.8409	Intermediate Similarity	NPC317030
0.8383	Intermediate Similarity	NPC194640
0.8382	Intermediate Similarity	NPC198339
0.8373	Intermediate Similarity	NPC279918
0.837	Intermediate Similarity	NPC98715
0.8365	Intermediate Similarity	NPC190296
0.8333	Intermediate Similarity	NPC233936
0.8333	Intermediate Similarity	NPC302191
0.8305	Intermediate Similarity	NPC204565
0.8304	Intermediate Similarity	NPC34508
0.8304	Intermediate Similarity	NPC314603
0.8289	Intermediate Similarity	NPC127677
0.8289	Intermediate Similarity	NPC258062
0.8287	Intermediate Similarity	NPC11445
0.8286	Intermediate Similarity	NPC163055
0.8282	Intermediate Similarity	NPC105818
0.8282	Intermediate Similarity	NPC24678
0.8278	Intermediate Similarity	NPC474177
0.8266	Intermediate Similarity	NPC59269
0.8263	Intermediate Similarity	NPC131718
0.8258	Intermediate Similarity	NPC173028
0.8258	Intermediate Similarity	NPC65215
0.8256	Intermediate Similarity	NPC189812
0.8256	Intermediate Similarity	NPC329688
0.8242	Intermediate Similarity	NPC229332
0.8235	Intermediate Similarity	NPC46225
0.8235	Intermediate Similarity	NPC225821
0.8232	Intermediate Similarity	NPC157828
0.8232	Intermediate Similarity	NPC195239
0.8222	Intermediate Similarity	NPC47190
0.8204	Intermediate Similarity	NPC318065
0.8204	Intermediate Similarity	NPC56765
0.8204	Intermediate Similarity	NPC206819
0.8192	Intermediate Similarity	NPC163421
0.8192	Intermediate Similarity	NPC188387
0.8161	Intermediate Similarity	NPC248454
0.8148	Intermediate Similarity	NPC159856
0.8146	Intermediate Similarity	NPC474707
0.8136	Intermediate Similarity	NPC165201
0.8132	Intermediate Similarity	NPC133366
0.8125	Intermediate Similarity	NPC469767
0.8125	Intermediate Similarity	NPC469779
0.8125	Intermediate Similarity	NPC469783
0.8125	Intermediate Similarity	NPC469768
0.8125	Intermediate Similarity	NPC469780
0.8125	Intermediate Similarity	NPC469784
0.8125	Intermediate Similarity	NPC469761
0.8114	Intermediate Similarity	NPC270009
0.8101	Intermediate Similarity	NPC119700
0.8101	Intermediate Similarity	NPC261195
0.8101	Intermediate Similarity	NPC29886
0.8098	Intermediate Similarity	NPC477044
0.8098	Intermediate Similarity	NPC477041
0.8095	Intermediate Similarity	NPC135141
0.8095	Intermediate Similarity	NPC92796
0.8084	Intermediate Similarity	NPC285469
0.8083	Intermediate Similarity	NPC204491
0.8083	Intermediate Similarity	NPC203614
0.8079	Intermediate Similarity	NPC469358
0.8075	Intermediate Similarity	NPC469766
0.8063	Intermediate Similarity	NPC73767
0.8061	Intermediate Similarity	NPC53947
0.8056	Intermediate Similarity	NPC34271
0.8054	Intermediate Similarity	NPC477045
0.8053	Intermediate Similarity	NPC271862
0.805	Intermediate Similarity	NPC84911
0.8049	Intermediate Similarity	NPC471957
0.8045	Intermediate Similarity	NPC315555
0.8035	Intermediate Similarity	NPC470498
0.8023	Intermediate Similarity	NPC71037
0.8023	Intermediate Similarity	NPC317430
0.8023	Intermediate Similarity	NPC192270
0.8023	Intermediate Similarity	NPC78020
0.8021	Intermediate Similarity	NPC151976
0.8021	Intermediate Similarity	NPC87856
0.8011	Intermediate Similarity	NPC252338
0.8011	Intermediate Similarity	NPC206967
0.8011	Intermediate Similarity	NPC6093
0.8	Intermediate Similarity	NPC265576
0.8	Intermediate Similarity	NPC16667
0.799	Intermediate Similarity	NPC132211
0.7989	Intermediate Similarity	NPC472123
0.7989	Intermediate Similarity	NPC15102
0.7987	Intermediate Similarity	NPC96102
0.7979	Intermediate Similarity	NPC267965
0.7979	Intermediate Similarity	NPC475602
0.7978	Intermediate Similarity	NPC48938
0.7955	Intermediate Similarity	NPC293472
0.795	Intermediate Similarity	NPC110126
0.7946	Intermediate Similarity	NPC227582
0.7944	Intermediate Similarity	NPC94752
0.7943	Intermediate Similarity	NPC472586
0.7937	Intermediate Similarity	NPC105127
0.7937	Intermediate Similarity	NPC477043
0.7929	Intermediate Similarity	NPC129721
0.7926	Intermediate Similarity	NPC193761
0.7923	Intermediate Similarity	NPC99666
0.7917	Intermediate Similarity	NPC207726
0.7917	Intermediate Similarity	NPC470507
0.791	Intermediate Similarity	NPC472443
0.7907	Intermediate Similarity	NPC470508
0.7906	Intermediate Similarity	NPC314957
0.7898	Intermediate Similarity	NPC267885
0.7892	Intermediate Similarity	NPC205403
0.7889	Intermediate Similarity	NPC476319
0.7889	Intermediate Similarity	NPC280290
0.788	Intermediate Similarity	NPC267343
0.7879	Intermediate Similarity	NPC288838
0.7877	Intermediate Similarity	NPC139291
0.7877	Intermediate Similarity	NPC472108
0.7874	Intermediate Similarity	NPC280548
0.7849	Intermediate Similarity	NPC90723
0.7848	Intermediate Similarity	NPC82295
0.7845	Intermediate Similarity	NPC235684
0.7845	Intermediate Similarity	NPC171171
0.7844	Intermediate Similarity	NPC33421
0.7841	Intermediate Similarity	NPC203468
0.7841	Intermediate Similarity	NPC149155
0.7841	Intermediate Similarity	NPC110500
0.7838	Intermediate Similarity	NPC181502
0.7838	Intermediate Similarity	NPC85066
0.7836	Intermediate Similarity	NPC215584
0.7836	Intermediate Similarity	NPC44773
0.7833	Intermediate Similarity	NPC204717
0.7833	Intermediate Similarity	NPC472294
0.7831	Intermediate Similarity	NPC476874
0.7826	Intermediate Similarity	NPC324149
0.7824	Intermediate Similarity	NPC216643
0.7809	Intermediate Similarity	NPC126709
0.7809	Intermediate Similarity	NPC248041
0.7809	Intermediate Similarity	NPC55772
0.78	Intermediate Similarity	NPC147446
0.7798	Intermediate Similarity	NPC216713
0.7797	Intermediate Similarity	NPC203754
0.7797	Intermediate Similarity	NPC150048
0.7796	Intermediate Similarity	NPC231342
0.7791	Intermediate Similarity	NPC279081
0.779	Intermediate Similarity	NPC314002
0.7784	Intermediate Similarity	NPC37548
0.7778	Intermediate Similarity	NPC472109
0.7778	Intermediate Similarity	NPC472110
0.7778	Intermediate Similarity	NPC67056
0.7778	Intermediate Similarity	NPC472444
0.7778	Intermediate Similarity	NPC475506
0.7778	Intermediate Similarity	NPC220765
0.7765	Intermediate Similarity	NPC51054
0.7761	Intermediate Similarity	NPC141428
0.7761	Intermediate Similarity	NPC235885
0.776	Intermediate Similarity	NPC321708
0.776	Intermediate Similarity	NPC213629
0.776	Intermediate Similarity	NPC323927
0.7753	Intermediate Similarity	NPC111275
0.7751	Intermediate Similarity	NPC200214
0.7751	Intermediate Similarity	NPC325903
0.7749	Intermediate Similarity	NPC470500
0.7747	Intermediate Similarity	NPC99428
0.7737	Intermediate Similarity	NPC155143
0.7737	Intermediate Similarity	NPC260900

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 NPC151939 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	211
0.1-0.2	547
0.2-0.3	685
0.3-0.4	1678
0.4-0.5	2819
0.5-0.6	2044
0.6-0.7	943
0.7-0.8	209
0.8-0.85	14
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8647	High Similarity	NPD4079	Approved
0.8647	High Similarity	NPD4076	Approved
0.8588	High Similarity	NPD3506	Approved
0.8588	High Similarity	NPD3505	Approved
0.8415	Intermediate Similarity	NPD6026	Approved
0.8402	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8382	Intermediate Similarity	NPD6595	Phase 3
0.8363	Intermediate Similarity	NPD5065	Approved
0.8305	Intermediate Similarity	NPD8431	Approved
0.8235	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8192	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD2144	Approved
0.8161	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4638	Approved
0.8129	Intermediate Similarity	NPD4640	Approved
0.8129	Intermediate Similarity	NPD4639	Approved
0.8125	Intermediate Similarity	NPD3038	Discontinued
0.8118	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD1722	Approved
0.8063	Intermediate Similarity	NPD786	Approved
0.8061	Intermediate Similarity	NPD2172	Phase 1
0.8059	Intermediate Similarity	NPD3323	Discontinued
0.8057	Intermediate Similarity	NPD4181	Approved
0.8	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3100	Discontinued
0.8	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.7989	Intermediate Similarity	NPD7957	Phase 1
0.7989	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.7978	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7956	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD4128	Approved
0.7906	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7898	Intermediate Similarity	NPD4075	Phase 2
0.7898	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.788	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD1325	Approved
0.7874	Intermediate Similarity	NPD1326	Approved
0.7849	Intermediate Similarity	NPD7948	Phase 1
0.7844	Intermediate Similarity	NPD4463	Approved
0.7844	Intermediate Similarity	NPD4462	Approved
0.7841	Intermediate Similarity	NPD482	Approved
0.7831	Intermediate Similarity	NPD4702	Approved
0.7831	Intermediate Similarity	NPD4703	Approved
0.7829	Intermediate Similarity	NPD3609	Approved
0.7829	Intermediate Similarity	NPD3610	Approved
0.7802	Intermediate Similarity	NPD3486	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD2092	Phase 2
0.7778	Intermediate Similarity	NPD2094	Phase 2
0.7778	Intermediate Similarity	NPD2095	Phase 2
0.7746	Intermediate Similarity	NPD6635	Approved
0.7735	Intermediate Similarity	NPD2096	Phase 2
0.7735	Intermediate Similarity	NPD2091	Phase 2
0.7727	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7714	Intermediate Similarity	NPD5021	Discontinued
0.7705	Intermediate Similarity	NPD3961	Discontinued
0.7684	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.768	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7665	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7654	Intermediate Similarity	NPD8122	Approved
0.7654	Intermediate Similarity	NPD8123	Approved
0.7651	Intermediate Similarity	NPD5254	Discontinued
0.7647	Intermediate Similarity	NPD2837	Discontinued
0.7634	Intermediate Similarity	NPD3404	Approved
0.7632	Intermediate Similarity	NPD4601	Approved
0.7632	Intermediate Similarity	NPD4600	Approved
0.7622	Intermediate Similarity	NPD6281	Approved
0.7614	Intermediate Similarity	NPD2641	Approved
0.7614	Intermediate Similarity	NPD2640	Approved
0.7614	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.7611	Intermediate Similarity	NPD8386	Phase 2
0.7604	Intermediate Similarity	NPD8072	Approved
0.7598	Intermediate Similarity	NPD2381	Approved
0.7598	Intermediate Similarity	NPD2380	Approved
0.7598	Intermediate Similarity	NPD2382	Approved
0.7594	Intermediate Similarity	NPD1038	Approved
0.7586	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD750	Phase 2
0.7581	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD5426	Phase 3
0.7552	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD2928	Phase 2
0.7541	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.754	Intermediate Similarity	NPD6619	Phase 3
0.7529	Intermediate Similarity	NPD1404	Approved
0.7529	Intermediate Similarity	NPD1403	Approved
0.7526	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD3717	Discontinued
0.7474	Intermediate Similarity	NPD5901	Discontinued
0.7474	Intermediate Similarity	NPD8272	Phase 2
0.7474	Intermediate Similarity	NPD6664	Approved
0.7473	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7461	Intermediate Similarity	NPD8073	Approved
0.746	Intermediate Similarity	NPD7618	Phase 3
0.746	Intermediate Similarity	NPD7619	Phase 3
0.746	Intermediate Similarity	NPD7944	Discontinued
0.7458	Intermediate Similarity	NPD2642	Approved
0.7458	Intermediate Similarity	NPD2639	Approved
0.7457	Intermediate Similarity	NPD2580	Discontinued
0.7456	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7437	Intermediate Similarity	NPD8094	Discontinued
0.7425	Intermediate Similarity	NPD1592	Phase 3
0.7424	Intermediate Similarity	NPD5067	Phase 2
0.7424	Intermediate Similarity	NPD5066	Phase 2
0.7424	Intermediate Similarity	NPD7470	Discontinued
0.7419	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7419	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7416	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7409	Intermediate Similarity	NPD4511	Phase 1
0.7403	Intermediate Similarity	NPD5100	Phase 3
0.7398	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7398	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD3825	Phase 3
0.7387	Intermediate Similarity	NPD8093	Discontinued
0.7386	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD7234	Approved
0.738	Intermediate Similarity	NPD7233	Approved
0.7374	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7374	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD6217	Discontinued
0.7366	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.734	Intermediate Similarity	NPD4499	Approved
0.7322	Intermediate Similarity	NPD6555	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD5862	Discovery
0.7316	Intermediate Similarity	NPD802	Phase 2
0.7312	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4547	Phase 3
0.7306	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5912	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD5913	Phase 3
0.7297	Intermediate Similarity	NPD5596	Phase 2
0.7291	Intermediate Similarity	NPD8405	Clinical (unspecified phase)
0.7288	Intermediate Similarity	NPD5315	Discontinued
0.7286	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD2882	Phase 1
0.7283	Intermediate Similarity	NPD6476	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD6158	Phase 2
0.7277	Intermediate Similarity	NPD5612	Discontinued
0.7273	Intermediate Similarity	NPD5255	Approved
0.7258	Intermediate Similarity	NPD6178	Phase 3
0.7251	Intermediate Similarity	NPD1683	Approved
0.725	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7247	Intermediate Similarity	NPD5140	Approved
0.7247	Intermediate Similarity	NPD5138	Approved
0.7239	Intermediate Similarity	NPD3476	Approved
0.7239	Intermediate Similarity	NPD3475	Approved
0.7238	Intermediate Similarity	NPD3116	Approved
0.7238	Intermediate Similarity	NPD3117	Approved
0.7222	Intermediate Similarity	NPD8410	Clinical (unspecified phase)
0.7216	Intermediate Similarity	NPD5541	Clinical (unspecified phase)
0.7214	Intermediate Similarity	NPD3330	Phase 1
0.7214	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7212	Intermediate Similarity	NPD3385	Approved
0.7204	Intermediate Similarity	NPD5522	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD5105	Approved
0.7204	Intermediate Similarity	NPD5106	Approved
0.7194	Intermediate Similarity	NPD7187	Phase 2
0.7194	Intermediate Similarity	NPD6975	Discontinued
0.7192	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD7824	Approved
0.7186	Intermediate Similarity	NPD2509	Approved
0.7186	Intermediate Similarity	NPD2510	Approved
0.7184	Intermediate Similarity	NPD3262	Approved
0.7179	Intermediate Similarity	NPD6479	Discontinued
0.7179	Intermediate Similarity	NPD484	Approved
0.7179	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD4880	Discontinued
0.7163	Intermediate Similarity	NPD7271	Approved
0.716	Intermediate Similarity	NPD2119	Approved
0.716	Intermediate Similarity	NPD2118	Approved
0.7159	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7151	Intermediate Similarity	NPD8408	Discontinued
0.7143	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7136	Intermediate Similarity	NPD1392	Approved
0.7135	Intermediate Similarity	NPD8036	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD8037	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD6987	Phase 1
0.712	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4670	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD2581	Approved
0.7119	Intermediate Similarity	NPD2582	Approved
0.7119	Intermediate Similarity	NPD4671	Clinical (unspecified phase)
0.7119	Intermediate Similarity	NPD4669	Clinical (unspecified phase)
0.7113	Intermediate Similarity	NPD5003	Discontinued
0.711	Intermediate Similarity	NPD1661	Suspended
0.7108	Intermediate Similarity	NPD3393	Approved
0.7108	Intermediate Similarity	NPD3394	Approved
0.7108	Intermediate Similarity	NPD4029	Approved
0.7108	Intermediate Similarity	NPD4030	Approved
0.7108	Intermediate Similarity	NPD4028	Approved
0.7108	Intermediate Similarity	NPD3389	Approved
0.7097	Intermediate Similarity	NPD5897	Approved
0.7097	Intermediate Similarity	NPD5898	Approved
0.7097	Intermediate Similarity	NPD5899	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