NPASS Compound

Structure

NPC52254 OpenBabel07101718332D 38 42 0 0 1 0 0 0 0 0999 V2000 -0.8660 -1.5000 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6824 3.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.2702 3.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6879 3.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8635 2.1045 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 -2.5981 2.5000 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 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2812 2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 2.5000 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 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8690 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -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 1 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -5.2812 1.1910 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 O 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 3 2 0 0 0 0 2 36 1 0 0 0 0 4 5 2 0 0 0 0 4 6 1 0 0 0 0 5 7 1 0 0 0 0 6 14 2 0 0 0 0 7 18 2 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 29 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 17 2 0 0 0 0 11 30 1 0 0 0 0 12 31 1 0 0 0 0 13 3 1 1 0 0 0 13 16 1 0 0 0 0 13 25 1 0 0 0 0 14 15 1 0 0 0 0 14 18 1 0 0 0 0 15 21 2 0 0 0 0 16 17 1 1 0 0 0 17 26 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 29 1 1 0 0 0 20 12 1 6 0 0 0 20 22 1 0 0 0 0 20 37 1 0 0 0 0 21 28 1 0 0 0 0 22 23 1 0 0 0 0 22 32 1 1 0 0 0 23 24 1 0 0 0 0 23 33 1 6 0 0 0 24 27 1 0 0 0 0 24 34 1 1 0 0 0 25 29 1 1 0 0 0 25 38 1 0 0 0 0 26 35 2 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 27 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	530.23
Volume:	515.416
LogP:	1.042
LogD:	0.812
LogS:	-2.777
# Rotatable Bonds:	8
TPSA:	161.78
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.143
Synthetic Accessibility Score:	5.115
Fsp3:	0.556
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.992
MDCK Permeability:	3.42E-05
Pgp-inhibitor:	0.006
Pgp-substrate:	0.845
Human Intestinal Absorption (HIA):	0.928
20% Bioavailability (F20%):	0.019
30% Bioavailability (F30%):	0.622

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.299
Plasma Protein Binding (PPB):	52.86%
Volume Distribution (VD):	0.619
Pgp-substrate:	49.26%

ADMET: Metabolism

CYP1A2-inhibitor:	0.046
CYP1A2-substrate:	0.377
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.351
CYP2C9-inhibitor:	0.003
CYP2C9-substrate:	0.095
CYP2D6-inhibitor:	0.005
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.089
CYP3A4-substrate:	0.554

ADMET: Excretion

Clearance (CL):	3.969
Half-life (T1/2):	0.809

ADMET: Toxicity

hERG Blockers:	0.107
Human Hepatotoxicity (H-HT):	0.144
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.19
Rat Oral Acute Toxicity:	0.361
Maximum Recommended Daily Dose:	0.965
Skin Sensitization:	0.534
Carcinogencity:	0.434
Eye Corrosion:	0.003
Eye Irritation:	0.013
Respiratory Toxicity:	0.976

Download Data

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

Natural Product: NPC52254

Natural Product ID:	NPC52254
*Common Name:**	Turbinatine
IUPAC Name:	methyl (Z)-2-[(2S,3S,4S,12bS)-3-ethenyl-4-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl]-3-hydroxyprop-2-enoate
Synonyms:	Turbinatine
Standard InCHIKey:	XAYUCVICBPYPRE-LPRPFWDGSA-N
Standard InCHI:	InChI=1S/C27H34N2O9/c1-3-13-16(17(11-30)26(35)36-2)10-19-21-15(14-6-4-5-7-18(14)28-21)8-9-29(19)25(13)38-27-24(34)23(33)22(32)20(12-31)37-27/h3-7,11,13,16,19-20,22-25,27-28,30-34H,1,8-10,12H2,2H3/b17-11-/t13-,16-,19-,20-,22-,23+,24-,25-,27+/m0/s1
SMILES:	OC[C@@H]1O[C@H](O[C@H]2[C@@H](C=C)[C@H](C[C@@H]3N2CCc2c3[nH]c3c2cccc3)/C(=C/O)/C(=O)OC)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL452240
PubChem CID:	44559633
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0002750] Corynanthean-type alkaloids

*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
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15568781]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21341711]
NPO3893	Chimarrhis turbinata	Species	Rubiaceae	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	2
Others	2

Activity Type	# Activity
Individual Protein	1
Organism	2
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2749	Individual Protein	Acetylcholinesterase	Rattus norvegicus	IC50	=	1860.0	nM	PMID[547998]
NPT1	Others	Radical scavenging activity		IC50	=	50900.0	nM	PMID[547998]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	>	250.0	ug ml-1	PMID[547999]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	IC12	=	100.0	ug ml-1	PMID[547999]

☑ 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 NPC52254 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	259
0.1-0.2	1254
0.2-0.3	4223
0.3-0.4	16095
0.4-0.5	14476
0.5-0.6	3986
0.6-0.7	1934
0.7-0.8	397
0.8-0.85	43
0.85-0.9	13
0.9-0.95	13
0.95-1	4

Similarity Score	Similarity Level	Natural Product ID
0.9645	High Similarity	NPC82070
0.9444	High Similarity	NPC476114
0.9406	High Similarity	NPC475271
0.9254	High Similarity	NPC174788
0.904	High Similarity	NPC474905
0.8794	High Similarity	NPC476115
0.8737	High Similarity	NPC199851
0.8737	High Similarity	NPC312870
0.8737	High Similarity	NPC294909
0.8737	High Similarity	NPC128265
0.8737	High Similarity	NPC254240
0.8525	High Similarity	NPC57453
0.8513	High Similarity	NPC102338
0.8513	High Similarity	NPC63199
0.8513	High Similarity	NPC196251
0.8513	High Similarity	NPC111602
0.8418	Intermediate Similarity	NPC175474
0.8398	Intermediate Similarity	NPC477548
0.8276	Intermediate Similarity	NPC49196
0.8276	Intermediate Similarity	NPC313985
0.8276	Intermediate Similarity	NPC249150
0.8276	Intermediate Similarity	NPC79129
0.8276	Intermediate Similarity	NPC81654
0.8276	Intermediate Similarity	NPC195461
0.8267	Intermediate Similarity	NPC52557
0.8259	Intermediate Similarity	NPC245916
0.8191	Intermediate Similarity	NPC469501
0.8191	Intermediate Similarity	NPC469470
0.8191	Intermediate Similarity	NPC472112
0.8177	Intermediate Similarity	NPC50503
0.8163	Intermediate Similarity	NPC472108
0.8163	Intermediate Similarity	NPC139291
0.8152	Intermediate Similarity	NPC221100
0.8152	Intermediate Similarity	NPC234078
0.8119	Intermediate Similarity	NPC19692
0.8119	Intermediate Similarity	NPC220151
0.8113	Intermediate Similarity	NPC313640
0.8109	Intermediate Similarity	NPC472113
0.8079	Intermediate Similarity	NPC473800
0.806	Intermediate Similarity	NPC472097
0.8028	Intermediate Similarity	NPC21638
0.7919	Intermediate Similarity	NPC33949
0.791	Intermediate Similarity	NPC472323
0.7889	Intermediate Similarity	NPC472110
0.7889	Intermediate Similarity	NPC472109
0.7824	Intermediate Similarity	NPC148183
0.7824	Intermediate Similarity	NPC152768
0.782	Intermediate Similarity	NPC238457
0.7789	Intermediate Similarity	NPC15840
0.7767	Intermediate Similarity	NPC289299
0.7767	Intermediate Similarity	NPC57994
0.7761	Intermediate Similarity	NPC258480
0.7752	Intermediate Similarity	NPC281049
0.7727	Intermediate Similarity	NPC472122
0.7727	Intermediate Similarity	NPC24594
0.7723	Intermediate Similarity	NPC79062
0.7723	Intermediate Similarity	NPC472107
0.7716	Intermediate Similarity	NPC472123
0.7711	Intermediate Similarity	NPC472104
0.7703	Intermediate Similarity	NPC50997
0.7703	Intermediate Similarity	NPC160127
0.7685	Intermediate Similarity	NPC66210
0.7682	Intermediate Similarity	NPC472099
0.767	Intermediate Similarity	NPC55493
0.7653	Intermediate Similarity	NPC317430
0.765	Intermediate Similarity	NPC219336
0.7626	Intermediate Similarity	NPC312645
0.7626	Intermediate Similarity	NPC249428
0.7624	Intermediate Similarity	NPC143533
0.7621	Intermediate Similarity	NPC473105
0.7619	Intermediate Similarity	NPC241024
0.7615	Intermediate Similarity	NPC191489
0.7612	Intermediate Similarity	NPC469896
0.7612	Intermediate Similarity	NPC187827
0.7612	Intermediate Similarity	NPC472105
0.76	Intermediate Similarity	NPC15573
0.76	Intermediate Similarity	NPC217372
0.76	Intermediate Similarity	NPC183662
0.7589	Intermediate Similarity	NPC472762
0.7586	Intermediate Similarity	NPC472119
0.7574	Intermediate Similarity	NPC113626
0.7573	Intermediate Similarity	NPC284685
0.757	Intermediate Similarity	NPC277350
0.7569	Intermediate Similarity	NPC472291
0.7546	Intermediate Similarity	NPC469743
0.7534	Intermediate Similarity	NPC274842
0.7512	Intermediate Similarity	NPC476874
0.7512	Intermediate Similarity	NPC478077
0.75	Intermediate Similarity	NPC475720
0.75	Intermediate Similarity	NPC474192
0.75	Intermediate Similarity	NPC271797
0.75	Intermediate Similarity	NPC21174
0.75	Intermediate Similarity	NPC214428
0.749	Intermediate Similarity	NPC100734
0.749	Intermediate Similarity	NPC315634
0.749	Intermediate Similarity	NPC88923
0.7489	Intermediate Similarity	NPC89508
0.7489	Intermediate Similarity	NPC306644
0.7489	Intermediate Similarity	NPC236424
0.7488	Intermediate Similarity	NPC18661
0.7476	Intermediate Similarity	NPC328798
0.7476	Intermediate Similarity	NPC325775
0.7464	Intermediate Similarity	NPC472210
0.7464	Intermediate Similarity	NPC247735
0.7464	Intermediate Similarity	NPC81802
0.7464	Intermediate Similarity	NPC472295
0.7464	Intermediate Similarity	NPC269886
0.7452	Intermediate Similarity	NPC127647
0.7443	Intermediate Similarity	NPC244856
0.7431	Intermediate Similarity	NPC234999
0.743	Intermediate Similarity	NPC162730
0.7427	Intermediate Similarity	NPC235684
0.7426	Intermediate Similarity	NPC326575
0.7426	Intermediate Similarity	NPC234987
0.7409	Intermediate Similarity	NPC229348
0.7404	Intermediate Similarity	NPC329858
0.7404	Intermediate Similarity	NPC314333
0.7402	Intermediate Similarity	NPC71037
0.7397	Intermediate Similarity	NPC472846
0.7393	Intermediate Similarity	NPC472116
0.7385	Intermediate Similarity	NPC478158
0.7382	Intermediate Similarity	NPC475816
0.7376	Intermediate Similarity	NPC478157
0.7373	Intermediate Similarity	NPC244741
0.7364	Intermediate Similarity	NPC475778
0.7356	Intermediate Similarity	NPC182814
0.7349	Intermediate Similarity	NPC474116
0.7348	Intermediate Similarity	NPC89987
0.7345	Intermediate Similarity	NPC64216
0.7343	Intermediate Similarity	NPC315555
0.7336	Intermediate Similarity	NPC249040
0.7333	Intermediate Similarity	NPC2395
0.7327	Intermediate Similarity	NPC189812
0.7327	Intermediate Similarity	NPC474145
0.7327	Intermediate Similarity	NPC329688
0.7327	Intermediate Similarity	NPC475841
0.7324	Intermediate Similarity	NPC149708
0.7315	Intermediate Similarity	NPC165599
0.7304	Intermediate Similarity	NPC133261
0.7296	Intermediate Similarity	NPC184680
0.7285	Intermediate Similarity	NPC111732
0.7282	Intermediate Similarity	NPC469358
0.7282	Intermediate Similarity	NPC325093
0.7282	Intermediate Similarity	NPC327373
0.7282	Intermediate Similarity	NPC322043
0.7277	Intermediate Similarity	NPC469594
0.7273	Intermediate Similarity	NPC321592
0.7273	Intermediate Similarity	NPC54803
0.7265	Intermediate Similarity	NPC470785
0.7265	Intermediate Similarity	NPC470784
0.7264	Intermediate Similarity	NPC20593
0.726	Intermediate Similarity	NPC62749
0.7252	Intermediate Similarity	NPC54744
0.7249	Intermediate Similarity	NPC476492
0.7248	Intermediate Similarity	NPC472111
0.7248	Intermediate Similarity	NPC309498
0.7237	Intermediate Similarity	NPC235885
0.7235	Intermediate Similarity	NPC476098
0.723	Intermediate Similarity	NPC472293
0.723	Intermediate Similarity	NPC231342
0.7227	Intermediate Similarity	NPC162860
0.722	Intermediate Similarity	NPC477979
0.7212	Intermediate Similarity	NPC318020
0.7209	Intermediate Similarity	NPC472296
0.7209	Intermediate Similarity	NPC472297
0.7209	Intermediate Similarity	NPC192674
0.7208	Intermediate Similarity	NPC476516
0.7207	Intermediate Similarity	NPC151976
0.7207	Intermediate Similarity	NPC75634
0.7207	Intermediate Similarity	NPC264176
0.7207	Intermediate Similarity	NPC472098
0.7205	Intermediate Similarity	NPC79107
0.7205	Intermediate Similarity	NPC475424
0.7204	Intermediate Similarity	NPC129909
0.7198	Intermediate Similarity	NPC19679
0.7198	Intermediate Similarity	NPC472444
0.7196	Intermediate Similarity	NPC469736
0.7192	Intermediate Similarity	NPC161861
0.719	Intermediate Similarity	NPC46413
0.7188	Intermediate Similarity	NPC469928
0.7188	Intermediate Similarity	NPC330009
0.7186	Intermediate Similarity	NPC95240
0.7186	Intermediate Similarity	NPC322135
0.7186	Intermediate Similarity	NPC223409
0.7184	Intermediate Similarity	NPC91179
0.7183	Intermediate Similarity	NPC474121
0.7175	Intermediate Similarity	NPC471080
0.7175	Intermediate Similarity	NPC469592
0.7172	Intermediate Similarity	NPC476514
0.717	Intermediate Similarity	NPC472292
0.7167	Intermediate Similarity	NPC284888
0.7163	Intermediate Similarity	NPC102008
0.716	Intermediate Similarity	NPC472435
0.7156	Intermediate Similarity	NPC305984
0.7143	Intermediate Similarity	NPC472436
0.7143	Intermediate Similarity	NPC311906
0.7143	Intermediate Similarity	NPC100547
0.7136	Intermediate Similarity	NPC53344
0.7136	Intermediate Similarity	NPC477065
0.7136	Intermediate Similarity	NPC54420

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 NPC52254 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	163
0.1-0.2	461
0.2-0.3	613
0.3-0.4	1679
0.4-0.5	2997
0.5-0.6	2488
0.6-0.7	678
0.7-0.8	67
0.8-0.85	2
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8737	High Similarity	NPD4501	Approved
0.8737	High Similarity	NPD4500	Approved
0.8276	Intermediate Similarity	NPD4600	Approved
0.8276	Intermediate Similarity	NPD4601	Approved
0.7767	Intermediate Similarity	NPD4602	Approved
0.7706	Intermediate Similarity	NPD8326	Phase 3
0.7706	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7706	Intermediate Similarity	NPD8325	Phase 3
0.7615	Intermediate Similarity	NPD7708	Approved
0.7611	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7573	Intermediate Similarity	NPD7955	Approved
0.7573	Intermediate Similarity	NPD7956	Approved
0.7546	Intermediate Similarity	NPD4506	Discontinued
0.7523	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.7512	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.749	Intermediate Similarity	NPD7803	Approved
0.7453	Intermediate Similarity	NPD6249	Phase 2
0.7453	Intermediate Similarity	NPD6248	Phase 2
0.7441	Intermediate Similarity	NPD5003	Discontinued
0.7431	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD4885	Approved
0.7407	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7404	Intermediate Similarity	NPD4499	Approved
0.7399	Intermediate Similarity	NPD6770	Approved
0.7342	Intermediate Similarity	NPD3393	Approved
0.7342	Intermediate Similarity	NPD3394	Approved
0.7342	Intermediate Similarity	NPD3389	Approved
0.7327	Intermediate Similarity	NPD7957	Phase 1
0.7327	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7318	Intermediate Similarity	NPD7470	Discontinued
0.7306	Intermediate Similarity	NPD4520	Approved
0.7285	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2095	Phase 2
0.7282	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7282	Intermediate Similarity	NPD2092	Phase 2
0.7282	Intermediate Similarity	NPD2094	Phase 2
0.726	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD8423	Phase 2
0.726	Intermediate Similarity	NPD8399	Phase 1
0.7246	Intermediate Similarity	NPD2091	Phase 2
0.7246	Intermediate Similarity	NPD2096	Phase 2
0.7209	Intermediate Similarity	NPD6661	Clinical (unspecified phase)
0.7209	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7204	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD4334	Discontinued
0.7184	Intermediate Similarity	NPD5898	Approved
0.7184	Intermediate Similarity	NPD5897	Approved
0.7184	Intermediate Similarity	NPD5899	Approved
0.7182	Intermediate Similarity	NPD2509	Approved
0.7182	Intermediate Similarity	NPD2510	Approved
0.7163	Intermediate Similarity	NPD53	Approved
0.7163	Intermediate Similarity	NPD7778	Approved
0.7163	Intermediate Similarity	NPD7777	Approved
0.7156	Intermediate Similarity	NPD2565	Phase 2
0.7156	Intermediate Similarity	NPD2564	Approved
0.7156	Intermediate Similarity	NPD5487	Phase 1
0.7143	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7129	Intermediate Similarity	NPD2844	Phase 3
0.7123	Intermediate Similarity	NPD8114	Approved
0.7123	Intermediate Similarity	NPD8115	Approved
0.7116	Intermediate Similarity	NPD6206	Phase 1
0.7091	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD6261	Phase 3
0.7083	Intermediate Similarity	NPD8468	Phase 2
0.7078	Intermediate Similarity	NPD8072	Approved
0.7078	Intermediate Similarity	NPD6176	Phase 1
0.7073	Intermediate Similarity	NPD482	Approved
0.7064	Intermediate Similarity	NPD7727	Phase 2
0.7048	Intermediate Similarity	NPD7878	Phase 2
0.7048	Intermediate Similarity	NPD5075	Discontinued
0.7045	Intermediate Similarity	NPD5901	Discontinued
0.7039	Intermediate Similarity	NPD5104	Approved
0.7039	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7026	Intermediate Similarity	NPD7730	Approved
0.7026	Intermediate Similarity	NPD7731	Approved
0.7022	Intermediate Similarity	NPD3794	Approved
0.7022	Intermediate Similarity	NPD3795	Approved
0.7021	Intermediate Similarity	NPD7951	Approved
0.7021	Intermediate Similarity	NPD7791	Approved
0.7021	Intermediate Similarity	NPD7953	Approved
0.7021	Intermediate Similarity	NPD7790	Approved
0.7021	Intermediate Similarity	NPD7950	Approved
0.7021	Intermediate Similarity	NPD7952	Approved
0.7021	Intermediate Similarity	NPD7789	Approved
0.7014	Intermediate Similarity	NPD5444	Phase 1
0.7013	Intermediate Similarity	NPD7271	Approved
0.7009	Intermediate Similarity	NPD4315	Phase 2
0.7005	Intermediate Similarity	NPD4397	Phase 1
0.7005	Intermediate Similarity	NPD4987	Clinical (unspecified phase)
0.7005	Intermediate Similarity	NPD6641	Approved
0.7005	Intermediate Similarity	NPD6642	Approved
0.7	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD8289	Discontinued
0.698	Remote Similarity	NPD8370	Discontinued
0.6968	Remote Similarity	NPD56	Approved
0.6968	Remote Similarity	NPD8282	Approved
0.6968	Remote Similarity	NPD8283	Approved
0.6966	Remote Similarity	NPD8374	Phase 3
0.6966	Remote Similarity	NPD7824	Approved
0.6964	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6955	Remote Similarity	NPD8073	Approved
0.6948	Remote Similarity	NPD7234	Approved
0.6948	Remote Similarity	NPD7233	Approved
0.6944	Remote Similarity	NPD7944	Discontinued
0.6942	Remote Similarity	NPD6183	Clinical (unspecified phase)
0.6942	Remote Similarity	NPD43	Approved
0.6942	Remote Similarity	NPD750	Phase 2
0.6942	Remote Similarity	NPD6182	Approved
0.6937	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6926	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.692	Remote Similarity	NPD8329	Phase 3
0.6916	Remote Similarity	NPD4897	Phase 2
0.6909	Remote Similarity	NPD7817	Phase 1
0.6907	Remote Similarity	NPD7796	Approved
0.6907	Remote Similarity	NPD7797	Approved
0.6906	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.69	Remote Similarity	NPD5632	Approved
0.687	Remote Similarity	NPD7194	Discontinued
0.6864	Remote Similarity	NPD6479	Discontinued
0.6863	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD2915	Discontinued
0.6861	Remote Similarity	NPD3003	Approved
0.6857	Remote Similarity	NPD5482	Discontinued
0.6851	Remote Similarity	NPD7780	Approved
0.6851	Remote Similarity	NPD7781	Approved
0.6849	Remote Similarity	NPD7946	Pre-registration
0.6847	Remote Similarity	NPD2920	Discontinued
0.6844	Remote Similarity	NPD5835	Phase 3
0.6844	Remote Similarity	NPD6529	Discontinued
0.6844	Remote Similarity	NPD5834	Phase 3
0.684	Remote Similarity	NPD6178	Phase 3
0.6833	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6827	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6826	Remote Similarity	NPD6578	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD7716	Approved
0.6824	Remote Similarity	NPD7717	Approved
0.6822	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD8466	Approved
0.6822	Remote Similarity	NPD8467	Approved
0.6822	Remote Similarity	NPD8465	Approved
0.6818	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD8272	Phase 2
0.6816	Remote Similarity	NPD7396	Approved
0.6816	Remote Similarity	NPD3947	Discontinued
0.6816	Remote Similarity	NPD5426	Phase 3
0.6814	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6812	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6807	Remote Similarity	NPD7558	Phase 2
0.6803	Remote Similarity	NPD8375	Approved
0.68	Remote Similarity	NPD7666	Phase 3
0.68	Remote Similarity	NPD7665	Phase 2
0.6792	Remote Similarity	NPD5596	Phase 2
0.6791	Remote Similarity	NPD1534	Approved
0.6787	Remote Similarity	NPD8255	Phase 2
0.6784	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD8364	Approved
0.6784	Remote Similarity	NPD8363	Approved
0.6783	Remote Similarity	NPD8406	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6777	Remote Similarity	NPD5473	Discontinued
0.6776	Remote Similarity	NPD8358	Approved
0.6771	Remote Similarity	NPD3777	Phase 3
0.6767	Remote Similarity	NPD3280	Approved
0.6763	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6762	Remote Similarity	NPD5483	Clinical (unspecified phase)
0.6753	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD6716	Phase 1
0.6748	Remote Similarity	NPD8371	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD4203	Approved
0.6745	Remote Similarity	NPD4204	Approved
0.6742	Remote Similarity	NPD1768	Approved
0.6741	Remote Similarity	NPD8098	Approved
0.6738	Remote Similarity	NPD5507	Approved
0.6738	Remote Similarity	NPD5506	Approved
0.6737	Remote Similarity	NPD6164	Phase 2
0.6737	Remote Similarity	NPD6165	Phase 2
0.6736	Remote Similarity	NPD2921	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4373	Phase 2
0.6732	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.673	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6728	Remote Similarity	NPD5913	Phase 3
0.6726	Remote Similarity	NPD2916	Discontinued
0.6718	Remote Similarity	NPD8459	Approved
0.6718	Remote Similarity	NPD8425	Approved
0.6718	Remote Similarity	NPD8460	Approved
0.6718	Remote Similarity	NPD8426	Approved
0.6712	Remote Similarity	NPD7619	Phase 3
0.6712	Remote Similarity	NPD484	Approved
0.6712	Remote Similarity	NPD7618	Phase 3
0.6712	Remote Similarity	NPD4427	Phase 2
0.6711	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.671	Remote Similarity	NPD7823	Clinical (unspecified phase)
0.6709	Remote Similarity	NPD6995	Phase 1
0.6707	Remote Similarity	NPD8463	Approved
0.6696	Remote Similarity	NPD5903	Approved
0.6696	Remote Similarity	NPD5902	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