NPASS Compound

Structure

Physi-Chem Properties

Molecular Weight:	254.14
Volume:	268.668
LogP:	1.135
LogD:	1.617
LogS:	-1.69
# Rotatable Bonds:	1
TPSA:	39.26
# H-Bond Aceptor:	3
# H-Bond Donor:	2
# Rings:	4
# Heavy Atoms:	3

MedChem Properties

QED Drug-Likeness Score:	0.817
Synthetic Accessibility Score:	3.659
Fsp3:	0.375
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
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:	-5.068
MDCK Permeability:	7.72448220232036e-06
Pgp-inhibitor:	0.996
Pgp-substrate:	0.771
Human Intestinal Absorption (HIA):	0.008
20% Bioavailability (F20%):	0.327
30% Bioavailability (F30%):	0.003

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.782
Plasma Protein Binding (PPB):	56.060516357421875%
Volume Distribution (VD):	1.807
Pgp-substrate:	43.741451263427734%

ADMET: Metabolism

CYP1A2-inhibitor:	0.832
CYP1A2-substrate:	0.709
CYP2C19-inhibitor:	0.119
CYP2C19-substrate:	0.776
CYP2C9-inhibitor:	0.09
CYP2C9-substrate:	0.24
CYP2D6-inhibitor:	0.972
CYP2D6-substrate:	0.908
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.714

ADMET: Excretion

Clearance (CL):	13.795
Half-life (T1/2):	0.831

ADMET: Toxicity

hERG Blockers:	0.139
Human Hepatotoxicity (H-HT):	0.275
Drug-inuced Liver Injury (DILI):	0.152
AMES Toxicity:	0.858
Rat Oral Acute Toxicity:	0.908
Maximum Recommended Daily Dose:	0.971
Skin Sensitization:	0.917
Carcinogencity:	0.383
Eye Corrosion:	0.005
Eye Irritation:	0.085
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC37423

Natural Product ID:	NPC37423
*Common Name:**	[(6As,9R)-7-Methyl-6,6A,8,9-Tetrahydro-4H-Indolo[4,3-Fg]Quinoline-9-Yl]Methanol
IUPAC Name:	[(6aS,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-yl]methanol
Synonyms:
Standard InCHIKey:	BIXJFIJYBLJTMK-BMIGLBTASA-N
Standard InCHI:	InChI=1S/C16H18N2O/c1-18-8-10(9-19)5-13-12-3-2-4-14-16(12)11(7-17-14)6-15(13)18/h2-5,7,10,15,17,19H,6,8-9H2,1H3/t10-,15+/m1/s1
SMILES:	OC[C@H]1CN(C)[C@@H]2C(=C1)c1cccc3c1c(C2)c[nH]3
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1331189
PubChem CID:	6604277
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002679] Ergoline and derivatives [CHEMONTID:0002747] Clavines and derivatives

*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
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	DOI[10.1016/S0040-4020(97)00607-8]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	crude resin	Mexican	n.a.	PMID[16562846]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19435339]
NPO31062	Pharbitis nil	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[23815260]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8496705]
NPO7268	Ipomoea violacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31062	Pharbitis nil	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[HerDing]
NPO2695	Ipomoea argyrophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2695	Ipomoea argyrophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7268	Ipomoea violacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31062	Pharbitis nil	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7268	Ipomoea violacea	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2695	Ipomoea argyrophylla	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO24622	Ipomoea tricolor	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17039	Pharbitis nil	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7268	Ipomoea violacea	Species	Convolvulaceae	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
AC50	3
Potency	14

Activity Type	# Activity
Individual Protein	16
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT149	Individual Protein	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Homo sapiens	Potency	=	12589.3	nM	PMID[496509]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	14125.4	nM	PMID[496509]
NPT211	Individual Protein	Hypoxia-inducible factor 1 alpha	Homo sapiens	Potency	=	3162.3	nM	PMID[496509]
NPT151	Individual Protein	15-hydroxyprostaglandin dehydrogenase [NAD+]	Homo sapiens	Potency	=	12589.3	nM	PMID[496509]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	Potency	=	125.9	nM	PMID[496509]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	Potency	=	12589.3	nM	PMID[496509]
NPT5	Individual Protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	3548.1	nM	PMID[496509]
NPT110	Individual Protein	Cytochrome P450 2D6	Homo sapiens	AC50	=	125.89	nM	PMID[496509]
NPT208	Individual Protein	Cytochrome P450 1A2	Homo sapiens	AC50	=	3981.07	nM	PMID[496509]
NPT109	Individual Protein	Cytochrome P450 3A4	Homo sapiens	AC50	=	12589.25	nM	PMID[496509]
NPT444	Individual Protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	31622.8	nM	PMID[496509]
NPT478	Individual Protein	Ataxin-2	Homo sapiens	Potency	n.a.	11220.2	nM	PMID[496509]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	12589.3	nM	PMID[496509]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	10000.0	nM	PMID[496509]

☑ 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 NPC37423 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	451
0.1-0.2	4475
0.2-0.3	20463
0.3-0.4	10510
0.4-0.5	3014
0.5-0.6	1925
0.6-0.7	1271
0.7-0.8	482
0.8-0.85	87
0.85-0.9	11
0.9-0.95	2
0.95-1	6

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC275305
0.9873	High Similarity	NPC68354
0.9808	High Similarity	NPC194411
0.9688	High Similarity	NPC176199
0.9688	High Similarity	NPC215795
0.9236	High Similarity	NPC206819
0.9236	High Similarity	NPC318065
0.9059	High Similarity	NPC95783
0.8994	High Similarity	NPC56765
0.878	High Similarity	NPC201700
0.8758	High Similarity	NPC41257
0.875	High Similarity	NPC51054
0.8718	High Similarity	NPC314372
0.8696	High Similarity	NPC286427
0.869	High Similarity	NPC151939
0.8634	High Similarity	NPC469785
0.8606	High Similarity	NPC474561
0.8606	High Similarity	NPC49954
0.859	High Similarity	NPC190296
0.858	High Similarity	NPC469762
0.8554	High Similarity	NPC63751
0.8509	High Similarity	NPC469763
0.8509	High Similarity	NPC469786
0.8509	High Similarity	NPC469765
0.8509	High Similarity	NPC259644
0.8509	High Similarity	NPC25008
0.8509	High Similarity	NPC469760
0.8509	High Similarity	NPC73952
0.85	High Similarity	NPC105818
0.85	High Similarity	NPC24678
0.8494	Intermediate Similarity	NPC54988
0.8488	Intermediate Similarity	NPC19679
0.8485	Intermediate Similarity	NPC90723
0.8485	Intermediate Similarity	NPC311276
0.848	Intermediate Similarity	NPC300688
0.8457	Intermediate Similarity	NPC212376
0.8457	Intermediate Similarity	NPC75540
0.8457	Intermediate Similarity	NPC80597
0.8457	Intermediate Similarity	NPC70922
0.8457	Intermediate Similarity	NPC211572
0.8424	Intermediate Similarity	NPC282231
0.8402	Intermediate Similarity	NPC313791
0.8397	Intermediate Similarity	NPC73767
0.8385	Intermediate Similarity	NPC33421
0.8373	Intermediate Similarity	NPC194640
0.8373	Intermediate Similarity	NPC40779
0.8365	Intermediate Similarity	NPC159856
0.8364	Intermediate Similarity	NPC279918
0.8364	Intermediate Similarity	NPC44773
0.8364	Intermediate Similarity	NPC215584
0.8344	Intermediate Similarity	NPC469784
0.8344	Intermediate Similarity	NPC469783
0.8344	Intermediate Similarity	NPC469761
0.8344	Intermediate Similarity	NPC469779
0.8344	Intermediate Similarity	NPC469780
0.8344	Intermediate Similarity	NPC469768
0.8344	Intermediate Similarity	NPC469767
0.8343	Intermediate Similarity	NPC470498
0.8303	Intermediate Similarity	NPC230869
0.8303	Intermediate Similarity	NPC135141
0.8303	Intermediate Similarity	NPC92796
0.8291	Intermediate Similarity	NPC469766
0.828	Intermediate Similarity	NPC110126
0.8274	Intermediate Similarity	NPC160105
0.8272	Intermediate Similarity	NPC53947
0.8269	Intermediate Similarity	NPC84911
0.8263	Intermediate Similarity	NPC102423
0.8261	Intermediate Similarity	NPC471957
0.8256	Intermediate Similarity	NPC59269
0.8246	Intermediate Similarity	NPC189812
0.8246	Intermediate Similarity	NPC329688
0.8232	Intermediate Similarity	NPC470507
0.8232	Intermediate Similarity	NPC229332
0.8218	Intermediate Similarity	NPC233936
0.8205	Intermediate Similarity	NPC96102
0.8205	Intermediate Similarity	NPC29886
0.8205	Intermediate Similarity	NPC261195
0.8187	Intermediate Similarity	NPC314603
0.8171	Intermediate Similarity	NPC163055
0.8153	Intermediate Similarity	NPC105127
0.8144	Intermediate Similarity	NPC131718
0.8136	Intermediate Similarity	NPC474707
0.8125	Intermediate Similarity	NPC228835
0.8121	Intermediate Similarity	NPC38736
0.8103	Intermediate Similarity	NPC11126
0.8103	Intermediate Similarity	NPC213468
0.8098	Intermediate Similarity	NPC37548
0.809	Intermediate Similarity	NPC204565
0.809	Intermediate Similarity	NPC317030
0.8086	Intermediate Similarity	NPC143872
0.8086	Intermediate Similarity	NPC288838
0.8079	Intermediate Similarity	NPC15102
0.8072	Intermediate Similarity	NPC184476
0.807	Intermediate Similarity	NPC280548
0.8061	Intermediate Similarity	NPC200214
0.8047	Intermediate Similarity	NPC472587
0.8046	Intermediate Similarity	NPC248454
0.8045	Intermediate Similarity	NPC173028
0.8045	Intermediate Similarity	NPC65215
0.8024	Intermediate Similarity	NPC216643
0.8012	Intermediate Similarity	NPC317430
0.8	Intermediate Similarity	NPC216713
0.8	Intermediate Similarity	NPC470233
0.8	Intermediate Similarity	NPC279081
0.7988	Intermediate Similarity	NPC187951
0.7977	Intermediate Similarity	NPC472123
0.7977	Intermediate Similarity	NPC34508
0.7952	Intermediate Similarity	NPC325903
0.7949	Intermediate Similarity	NPC82295
0.7933	Intermediate Similarity	NPC94752
0.7927	Intermediate Similarity	NPC21605
0.7912	Intermediate Similarity	NPC47190
0.7907	Intermediate Similarity	NPC154293
0.7888	Intermediate Similarity	NPC230002
0.7885	Intermediate Similarity	NPC22079
0.7882	Intermediate Similarity	NPC16667
0.7879	Intermediate Similarity	NPC321911
0.7879	Intermediate Similarity	NPC124005
0.7877	Intermediate Similarity	NPC280290
0.7869	Intermediate Similarity	NPC474177
0.7861	Intermediate Similarity	NPC300183
0.7857	Intermediate Similarity	NPC285469
0.7853	Intermediate Similarity	NPC242556
0.7849	Intermediate Similarity	NPC49217
0.784	Intermediate Similarity	NPC473868
0.784	Intermediate Similarity	NPC63157
0.7829	Intermediate Similarity	NPC293216
0.7826	Intermediate Similarity	NPC294693
0.7826	Intermediate Similarity	NPC133366
0.7818	Intermediate Similarity	NPC469811
0.7818	Intermediate Similarity	NPC477134
0.7818	Intermediate Similarity	NPC179787
0.7818	Intermediate Similarity	NPC201380
0.7812	Intermediate Similarity	NPC314102
0.7812	Intermediate Similarity	NPC251722
0.7797	Intermediate Similarity	NPC270009
0.7791	Intermediate Similarity	NPC470508
0.779	Intermediate Similarity	NPC17059
0.7784	Intermediate Similarity	NPC475602
0.7778	Intermediate Similarity	NPC59084
0.7765	Intermediate Similarity	NPC48938
0.7765	Intermediate Similarity	NPC475990
0.7764	Intermediate Similarity	NPC169433
0.7758	Intermediate Similarity	NPC63545
0.775	Intermediate Similarity	NPC325252
0.7722	Intermediate Similarity	NPC165495
0.7722	Intermediate Similarity	NPC475450
0.7719	Intermediate Similarity	NPC473320
0.7719	Intermediate Similarity	NPC122141
0.7716	Intermediate Similarity	NPC312092
0.7716	Intermediate Similarity	NPC88097
0.7714	Intermediate Similarity	NPC6982
0.7713	Intermediate Similarity	NPC470497
0.7709	Intermediate Similarity	NPC192270
0.7709	Intermediate Similarity	NPC71037
0.7708	Intermediate Similarity	NPC314957
0.7702	Intermediate Similarity	NPC150259
0.7701	Intermediate Similarity	NPC473640
0.7701	Intermediate Similarity	NPC265576
0.7692	Intermediate Similarity	NPC34844
0.7692	Intermediate Similarity	NPC207726
0.7692	Intermediate Similarity	NPC471458
0.7688	Intermediate Similarity	NPC198988
0.7684	Intermediate Similarity	NPC280852
0.7684	Intermediate Similarity	NPC98715
0.7684	Intermediate Similarity	NPC267885
0.768	Intermediate Similarity	NPC99939
0.768	Intermediate Similarity	NPC163421
0.768	Intermediate Similarity	NPC188387
0.768	Intermediate Similarity	NPC308931
0.7679	Intermediate Similarity	NPC470823
0.7669	Intermediate Similarity	NPC2949
0.7667	Intermediate Similarity	NPC139291
0.7667	Intermediate Similarity	NPC472108
0.7661	Intermediate Similarity	NPC67056
0.7661	Intermediate Similarity	NPC6436
0.7658	Intermediate Similarity	NPC475428
0.7651	Intermediate Similarity	NPC129042
0.765	Intermediate Similarity	NPC213629
0.765	Intermediate Similarity	NPC155444
0.764	Intermediate Similarity	NPC218268
0.7634	Intermediate Similarity	NPC157828
0.7634	Intermediate Similarity	NPC195239
0.7633	Intermediate Similarity	NPC141926
0.7632	Intermediate Similarity	NPC193761
0.763	Intermediate Similarity	NPC317105
0.7627	Intermediate Similarity	NPC110500
0.7627	Intermediate Similarity	NPC149155
0.7627	Intermediate Similarity	NPC203468
0.7624	Intermediate Similarity	NPC472294
0.7611	Intermediate Similarity	NPC470677
0.761	Intermediate Similarity	NPC179365
0.7602	Intermediate Similarity	NPC129721
0.7602	Intermediate Similarity	NPC236711
0.76	Intermediate Similarity	NPC78020
0.7598	Intermediate Similarity	NPC126709
0.7598	Intermediate Similarity	NPC248041
0.7595	Intermediate Similarity	NPC473587
0.7594	Intermediate Similarity	NPC11445
0.7593	Intermediate Similarity	NPC125746

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 NPC37423 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	248
0.1-0.2	612
0.2-0.3	1094
0.3-0.4	1635
0.4-0.5	2623
0.5-0.6	1942
0.6-0.7	809
0.7-0.8	155
0.8-0.85	20
0.85-0.9	7
0.9-0.95	3
0.95-1	2

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9873	High Similarity	NPD3506	Approved
0.9873	High Similarity	NPD3505	Approved
0.9811	High Similarity	NPD4076	Approved
0.9811	High Similarity	NPD4079	Approved
0.925	High Similarity	NPD4639	Approved
0.925	High Similarity	NPD4640	Approved
0.925	High Similarity	NPD4638	Approved
0.9024	High Similarity	NPD4128	Approved
0.897	High Similarity	NPD4075	Phase 2
0.8827	High Similarity	NPD3323	Discontinued
0.8802	High Similarity	NPD4181	Approved
0.8721	High Similarity	NPD3961	Discontinued
0.8671	High Similarity	NPD3100	Discontinued
0.8563	High Similarity	NPD3609	Approved
0.8563	High Similarity	NPD3610	Approved
0.8545	High Similarity	NPD5744	Clinical (unspecified phase)
0.8506	High Similarity	NPD3486	Clinical (unspecified phase)
0.8471	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.8443	Intermediate Similarity	NPD5021	Discontinued
0.8438	Intermediate Similarity	NPD4374	Clinical (unspecified phase)
0.8397	Intermediate Similarity	NPD786	Approved
0.8353	Intermediate Similarity	NPD5065	Approved
0.8333	Intermediate Similarity	NPD4779	Clinical (unspecified phase)
0.8304	Intermediate Similarity	NPD6375	Clinical (unspecified phase)
0.8294	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1722	Approved
0.8256	Intermediate Similarity	NPD2144	Approved
0.8229	Intermediate Similarity	NPD3607	Clinical (unspecified phase)
0.8218	Intermediate Similarity	NPD3038	Discontinued
0.8205	Intermediate Similarity	NPD198	Clinical (unspecified phase)
0.8187	Intermediate Similarity	NPD5254	Discontinued
0.8182	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.8176	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.8161	Intermediate Similarity	NPD6595	Phase 3
0.816	Intermediate Similarity	NPD2172	Phase 1
0.8132	Intermediate Similarity	NPD6664	Approved
0.809	Intermediate Similarity	NPD8431	Approved
0.8012	Intermediate Similarity	NPD2640	Approved
0.8012	Intermediate Similarity	NPD2641	Approved
0.8	Intermediate Similarity	NPD3943	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5315	Discontinued
0.7952	Intermediate Similarity	NPD2837	Discontinued
0.7939	Intermediate Similarity	NPD4463	Approved
0.7939	Intermediate Similarity	NPD4462	Approved
0.7933	Intermediate Similarity	NPD6217	Discontinued
0.7929	Intermediate Similarity	NPD1403	Approved
0.7929	Intermediate Similarity	NPD1404	Approved
0.7907	Intermediate Similarity	NPD2185	Clinical (unspecified phase)
0.7901	Intermediate Similarity	NPD6281	Approved
0.7866	Intermediate Similarity	NPD1683	Approved
0.7861	Intermediate Similarity	NPD1326	Approved
0.7861	Intermediate Similarity	NPD1325	Approved
0.7849	Intermediate Similarity	NPD2642	Approved
0.7849	Intermediate Similarity	NPD2639	Approved
0.7845	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7833	Intermediate Similarity	NPD4426	Clinical (unspecified phase)
0.7816	Intermediate Similarity	NPD5934	Clinical (unspecified phase)
0.7791	Intermediate Similarity	NPD4637	Clinical (unspecified phase)
0.7772	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.7765	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7753	Intermediate Similarity	NPD6277	Clinical (unspecified phase)
0.7711	Intermediate Similarity	NPD4703	Approved
0.7711	Intermediate Similarity	NPD4702	Approved
0.7711	Intermediate Similarity	NPD4547	Phase 3
0.7692	Intermediate Similarity	NPD5590	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD4550	Clinical (unspecified phase)
0.7688	Intermediate Similarity	NPD2960	Clinical (unspecified phase)
0.7674	Intermediate Similarity	NPD1853	Clinical (unspecified phase)
0.7668	Intermediate Similarity	NPD2125	Clinical (unspecified phase)
0.7667	Intermediate Similarity	NPD5105	Approved
0.7667	Intermediate Similarity	NPD5106	Approved
0.7663	Intermediate Similarity	NPD6180	Clinical (unspecified phase)
0.7647	Intermediate Similarity	NPD2580	Discontinued
0.7634	Intermediate Similarity	NPD7619	Phase 3
0.7634	Intermediate Similarity	NPD7618	Phase 3
0.7632	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.763	Intermediate Similarity	NPD3583	Phase 2
0.7627	Intermediate Similarity	NPD482	Approved
0.7622	Intermediate Similarity	NPD3404	Approved
0.7614	Intermediate Similarity	NPD3116	Approved
0.7614	Intermediate Similarity	NPD3117	Approved
0.7584	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7579	Intermediate Similarity	NPD4511	Phase 1
0.7569	Intermediate Similarity	NPD2095	Phase 2
0.7569	Intermediate Similarity	NPD2094	Phase 2
0.7569	Intermediate Similarity	NPD2092	Phase 2
0.7552	Intermediate Similarity	NPD5901	Discontinued
0.7544	Intermediate Similarity	NPD2748	Clinical (unspecified phase)
0.7528	Intermediate Similarity	NPD2928	Phase 2
0.7527	Intermediate Similarity	NPD2096	Phase 2
0.7527	Intermediate Similarity	NPD2091	Phase 2
0.7516	Intermediate Similarity	NPD4030	Approved
0.7516	Intermediate Similarity	NPD4028	Approved
0.7516	Intermediate Similarity	NPD3385	Approved
0.7516	Intermediate Similarity	NPD4029	Approved
0.7514	Intermediate Similarity	NPD5145	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7513	Intermediate Similarity	NPD7957	Phase 1
0.7513	Intermediate Similarity	NPD8094	Discontinued
0.75	Intermediate Similarity	NPD8072	Approved
0.7485	Intermediate Similarity	NPD977	Approved
0.7485	Intermediate Similarity	NPD975	Approved
0.7485	Intermediate Similarity	NPD976	Approved
0.7472	Intermediate Similarity	NPD750	Phase 2
0.7468	Intermediate Similarity	NPD2118	Approved
0.7468	Intermediate Similarity	NPD2119	Approved
0.7463	Intermediate Similarity	NPD7781	Approved
0.7463	Intermediate Similarity	NPD7780	Approved
0.7462	Intermediate Similarity	NPD8093	Discontinued
0.7461	Intermediate Similarity	NPD8272	Phase 2
0.746	Intermediate Similarity	NPD7948	Phase 1
0.7438	Intermediate Similarity	NPD3475	Approved
0.7438	Intermediate Similarity	NPD3476	Approved
0.7436	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7435	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7433	Intermediate Similarity	NPD4615	Phase 2
0.7425	Intermediate Similarity	NPD1918	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD3944	Approved
0.7407	Intermediate Similarity	NPD3942	Approved
0.7405	Intermediate Similarity	NPD2310	Clinical (unspecified phase)
0.7401	Intermediate Similarity	NPD5862	Discovery
0.7385	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.738	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7378	Intermediate Similarity	NPD1262	Discovery
0.7375	Intermediate Similarity	NPD3654	Approved
0.7371	Intermediate Similarity	NPD5426	Phase 3
0.7371	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7365	Intermediate Similarity	NPD3717	Discontinued
0.736	Intermediate Similarity	NPD5436	Phase 1
0.7358	Intermediate Similarity	NPD991	Phase 2
0.7358	Intermediate Similarity	NPD992	Clinical (unspecified phase)
0.7341	Intermediate Similarity	NPD2150	Discontinued
0.7337	Intermediate Similarity	NPD4957	Phase 2
0.7337	Intermediate Similarity	NPD7469	Discontinued
0.7333	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7326	Intermediate Similarity	NPD4499	Approved
0.7323	Intermediate Similarity	NPD7470	Discontinued
0.7317	Intermediate Similarity	NPD7271	Approved
0.7312	Intermediate Similarity	NPD3002	Clinical (unspecified phase)
0.7308	Intermediate Similarity	NPD8386	Phase 2
0.7303	Intermediate Similarity	NPD2390	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.73	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7424	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD45	Approved
0.7273	Intermediate Similarity	NPD6554	Approved
0.7268	Intermediate Similarity	NPD8073	Approved
0.7268	Intermediate Similarity	NPD5473	Discontinued
0.7268	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD2882	Phase 1
0.7262	Intermediate Similarity	NPD2006	Phase 2
0.7262	Intermediate Similarity	NPD2007	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD4601	Approved
0.7254	Intermediate Similarity	NPD4600	Approved
0.7251	Intermediate Similarity	NPD2430	Phase 2
0.7246	Intermediate Similarity	NPD7730	Approved
0.7246	Intermediate Similarity	NPD7731	Approved
0.7243	Intermediate Similarity	NPD7564	Discontinued
0.7241	Intermediate Similarity	NPD3114	Approved
0.7241	Intermediate Similarity	NPD3115	Approved
0.7241	Intermediate Similarity	NPD3113	Approved
0.7241	Intermediate Similarity	NPD6026	Approved
0.7241	Intermediate Similarity	NPD3112	Approved
0.7236	Intermediate Similarity	NPD4614	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6148	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5138	Approved
0.7232	Intermediate Similarity	NPD5140	Approved
0.7228	Intermediate Similarity	NPD1895	Discontinued
0.7228	Intermediate Similarity	NPD1708	Approved
0.7228	Intermediate Similarity	NPD4399	Phase 2
0.7228	Intermediate Similarity	NPD1707	Approved
0.7225	Intermediate Similarity	NPD2012	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD3813	Approved
0.7211	Intermediate Similarity	NPD1038	Approved
0.7211	Intermediate Similarity	NPD802	Phase 2
0.7202	Intermediate Similarity	NPD1592	Phase 3
0.72	Intermediate Similarity	NPD2865	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD4326	Phase 2
0.72	Intermediate Similarity	NPD3330	Phase 1
0.7198	Intermediate Similarity	NPD5100	Phase 3
0.7198	Intermediate Similarity	NPD2381	Approved
0.7198	Intermediate Similarity	NPD2380	Approved
0.7198	Intermediate Similarity	NPD2382	Approved
0.7193	Intermediate Similarity	NPD1661	Suspended
0.7191	Intermediate Similarity	NPD2720	Phase 1
0.7191	Intermediate Similarity	NPD2719	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD1332	Clinical (unspecified phase)
0.7189	Intermediate Similarity	NPD3320	Approved
0.7189	Intermediate Similarity	NPD3318	Approved
0.7189	Intermediate Similarity	NPD3319	Phase 1
0.7186	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD4051	Discontinued
0.7186	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7184	Intermediate Similarity	NPD2165	Phase 1
0.7177	Intermediate Similarity	NPD7824	Approved
0.7173	Intermediate Similarity	NPD7024	Clinical (unspecified phase)

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