NPASS Compound

Structure

NPC476429 OpenBabel07101719512D 41 47 0 0 1 0 0 0 0 0999 V2000 2.0857 -2.2071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7697 2.2105 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7805 4.4468 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1918 1.3869 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3695 3.9016 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6185 -1.9020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2197 -1.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0068 3.1977 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6295 3.5593 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0085 2.4776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2540 3.2008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7456 2.4471 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5854 0.9322 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6215 -0.1260 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4665 0.6838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6589 -0.4535 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2197 -0.7071 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7282 1.4472 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6330 2.1191 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7804 -0.4535 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2558 2.4807 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8900 0.7357 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6202 2.9319 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4600 1.4171 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9816 -0.1908 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.4774 2.4169 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5008 1.3416 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8536 0.9624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1218 0.9926 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.9782 -0.2077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7845 1.4151 0.0000 C 0 0 1 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 1.7921 2.0002 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.6589 0.0537 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 -1.8362 -0.0375 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6472 0.5356 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.6377 3.9318 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3172 0.9020 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3520 2.9017 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2874 -1.1587 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9964 1.4774 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 33 1 0 0 0 0 3 37 1 0 0 0 0 4 38 1 0 0 0 0 5 39 1 0 0 0 0 6 40 1 0 0 0 0 7 17 2 0 0 0 0 8 9 2 0 0 0 0 8 10 1 0 0 0 0 9 11 1 0 0 0 0 10 19 2 0 0 0 0 11 21 2 0 0 0 0 12 18 2 0 0 0 0 12 23 1 0 0 0 0 13 18 1 0 0 0 0 13 24 2 0 0 0 0 14 20 1 0 0 0 0 15 25 1 0 0 0 0 16 17 1 0 0 0 0 16 34 1 0 0 0 0 17 20 1 0 0 0 0 18 28 1 0 0 0 0 19 21 1 0 0 0 0 19 31 1 0 0 0 0 20 32 1 1 0 0 0 21 33 1 0 0 0 0 22 14 1 6 0 0 0 22 27 1 0 0 0 0 22 34 1 0 0 0 0 23 26 2 0 0 0 0 23 37 1 0 0 0 0 24 26 1 0 0 0 0 24 38 1 0 0 0 0 25 32 1 6 0 0 0 25 34 1 0 0 0 0 26 39 1 0 0 0 0 27 31 1 6 0 0 0 27 33 1 0 0 0 0 28 35 2 0 0 0 0 28 41 1 0 0 0 0 29 31 1 0 0 0 0 29 32 1 0 0 0 0 29 41 1 0 0 0 0 30 36 2 0 0 0 0 30 40 1 0 0 0 0 31 15 1 1 0 0 0 32 30 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	560.25
Volume:	561.93
LogP:	2.866
LogD:	3.07
LogS:	-4.851
# Rotatable Bonds:	8
TPSA:	86.77
# H-Bond Aceptor:	9
# H-Bond Donor:	0
# Rings:	8
# Heavy Atoms:	9

MedChem Properties

QED Drug-Likeness Score:	0.389
Synthetic Accessibility Score:	6.581
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.992
MDCK Permeability:	3.580134216463193e-05
Pgp-inhibitor:	0.779
Pgp-substrate:	0.265
Human Intestinal Absorption (HIA):	0.652
20% Bioavailability (F20%):	0.9
30% Bioavailability (F30%):	0.979

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.879
Plasma Protein Binding (PPB):	89.8410415649414%
Volume Distribution (VD):	1.196
Pgp-substrate:	7.83627986907959%

ADMET: Metabolism

CYP1A2-inhibitor:	0.066
CYP1A2-substrate:	0.681
CYP2C19-inhibitor:	0.73
CYP2C19-substrate:	0.914
CYP2C9-inhibitor:	0.486
CYP2C9-substrate:	0.48
CYP2D6-inhibitor:	0.615
CYP2D6-substrate:	0.877
CYP3A4-inhibitor:	0.962
CYP3A4-substrate:	0.922

ADMET: Excretion

Clearance (CL):	9.133
Half-life (T1/2):	0.071

ADMET: Toxicity

hERG Blockers:	0.011
Human Hepatotoxicity (H-HT):	0.205
Drug-inuced Liver Injury (DILI):	0.585
AMES Toxicity:	0.043
Rat Oral Acute Toxicity:	0.937
Maximum Recommended Daily Dose:	0.956
Skin Sensitization:	0.23
Carcinogencity:	0.791
Eye Corrosion:	0.003
Eye Irritation:	0.016
Respiratory Toxicity:	0.984

Download Data

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

Natural Product: NPC476429

Natural Product ID:	NPC476429
*Common Name:**	IFFBQMRDVLQSPU-QVUSUWOHSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	IFFBQMRDVLQSPU-QVUSUWOHSA-N
Standard InCHI:	InChI=1S/C32H36N2O7/c1-7-17-16-34-22-14-20(17)32(30(36)40-6)25(34)15-31(19-10-8-9-11-21(19)33(2)27(22)31)29(32)41-28(35)18-12-23(37-3)26(39-5)24(13-18)38-4/h7-13,20,22,25,27,29H,14-16H2,1-6H3/b17-7+/t20-,22-,25-,27+,29?,31+,32-/m0/s1
SMILES:	CC=C1CN2C3CC1C4(C2CC5(C3N(C6=CC=CC=C65)C)C4OC(=O)C7=CC(=C(C(=C7)OC)OC)OC)C(=O)OC
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL602441
PubChem CID:	46229138
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
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19191551]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	leaves	Purwodadi Botanical Garden, Indonesia	n.a.	PMID[20189404]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[22148233]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	Barks	n.a.	n.a.	PMID[23806072]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19678	Alstonia macrophylla	Species	Apocynaceae	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
Others	2

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT640	Individual Protein	Sodium/glucose cotransporter 1	Homo sapiens	Inhibition	=	7.2	%	PMID[572178]
NPT641	Individual Protein	Sodium/glucose cotransporter 2	Homo sapiens	Inhibition	=	47.6	%	PMID[572178]

☑ 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 NPC476429 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	433
0.1-0.2	1814
0.2-0.3	4883
0.3-0.4	11737
0.4-0.5	8545
0.5-0.6	13310
0.6-0.7	1791
0.7-0.8	175
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9756	High Similarity	NPC476436
0.8489	Intermediate Similarity	NPC304837
0.8489	Intermediate Similarity	NPC476258
0.8333	Intermediate Similarity	NPC113455
0.8311	Intermediate Similarity	NPC476220
0.8311	Intermediate Similarity	NPC160113
0.8304	Intermediate Similarity	NPC120239
0.8194	Intermediate Similarity	NPC154922
0.8	Intermediate Similarity	NPC191489
0.7942	Intermediate Similarity	NPC315634
0.7942	Intermediate Similarity	NPC100734
0.7942	Intermediate Similarity	NPC88923
0.787	Intermediate Similarity	NPC268077
0.7742	Intermediate Similarity	NPC207971
0.7737	Intermediate Similarity	NPC284685
0.7615	Intermediate Similarity	NPC328700
0.7615	Intermediate Similarity	NPC119818
0.7615	Intermediate Similarity	NPC202771
0.7615	Intermediate Similarity	NPC2173
0.7593	Intermediate Similarity	NPC71124
0.7561	Intermediate Similarity	NPC476425
0.7533	Intermediate Similarity	NPC195120
0.7533	Intermediate Similarity	NPC87560
0.7521	Intermediate Similarity	NPC139373
0.7511	Intermediate Similarity	NPC268223
0.7511	Intermediate Similarity	NPC223242
0.75	Intermediate Similarity	NPC82541
0.75	Intermediate Similarity	NPC220241
0.75	Intermediate Similarity	NPC295479
0.7489	Intermediate Similarity	NPC195636
0.7489	Intermediate Similarity	NPC231924
0.7477	Intermediate Similarity	NPC5374
0.7468	Intermediate Similarity	NPC131977
0.7467	Intermediate Similarity	NPC10732
0.7467	Intermediate Similarity	NPC118154
0.7467	Intermediate Similarity	NPC159815
0.7467	Intermediate Similarity	NPC157983
0.7467	Intermediate Similarity	NPC10653
0.7467	Intermediate Similarity	NPC318525
0.7464	Intermediate Similarity	NPC35680
0.7445	Intermediate Similarity	NPC234772
0.7437	Intermediate Similarity	NPC301501
0.7432	Intermediate Similarity	NPC476500
0.7431	Intermediate Similarity	NPC46744
0.7431	Intermediate Similarity	NPC14622
0.7431	Intermediate Similarity	NPC73020
0.7431	Intermediate Similarity	NPC124302
0.7431	Intermediate Similarity	NPC70290
0.7431	Intermediate Similarity	NPC215098
0.743	Intermediate Similarity	NPC208890
0.7418	Intermediate Similarity	NPC21425
0.7417	Intermediate Similarity	NPC469452
0.7407	Intermediate Similarity	NPC254957
0.7406	Intermediate Similarity	NPC469450
0.7391	Intermediate Similarity	NPC476069
0.7389	Intermediate Similarity	NPC116178
0.7368	Intermediate Similarity	NPC329992
0.7364	Intermediate Similarity	NPC226652
0.7364	Intermediate Similarity	NPC72788
0.7364	Intermediate Similarity	NPC314100
0.7364	Intermediate Similarity	NPC120671
0.7359	Intermediate Similarity	NPC128476
0.7357	Intermediate Similarity	NPC217903
0.7357	Intermediate Similarity	NPC321166
0.7355	Intermediate Similarity	NPC329932
0.7354	Intermediate Similarity	NPC80472
0.735	Intermediate Similarity	NPC473458
0.7344	Intermediate Similarity	NPC469451
0.7321	Intermediate Similarity	NPC476441
0.7321	Intermediate Similarity	NPC198160
0.7304	Intermediate Similarity	NPC182853
0.7304	Intermediate Similarity	NPC134702
0.7293	Intermediate Similarity	NPC38964
0.7292	Intermediate Similarity	NPC151171
0.7286	Intermediate Similarity	NPC476326
0.7284	Intermediate Similarity	NPC118189
0.7277	Intermediate Similarity	NPC248903
0.7269	Intermediate Similarity	NPC141440
0.7268	Intermediate Similarity	NPC26353
0.7265	Intermediate Similarity	NPC19175
0.7257	Intermediate Similarity	NPC473781
0.7257	Intermediate Similarity	NPC470631
0.7257	Intermediate Similarity	NPC476496
0.7257	Intermediate Similarity	NPC35390
0.7249	Intermediate Similarity	NPC148391
0.7244	Intermediate Similarity	NPC326895
0.7237	Intermediate Similarity	NPC127996
0.7235	Intermediate Similarity	NPC1820
0.7234	Intermediate Similarity	NPC26928
0.7232	Intermediate Similarity	NPC475147
0.7227	Intermediate Similarity	NPC475316
0.7227	Intermediate Similarity	NPC473486
0.7222	Intermediate Similarity	NPC162694
0.722	Intermediate Similarity	NPC286135
0.722	Intermediate Similarity	NPC473005
0.7212	Intermediate Similarity	NPC474858
0.7212	Intermediate Similarity	NPC94687
0.7212	Intermediate Similarity	NPC476495
0.7212	Intermediate Similarity	NPC106840
0.721	Intermediate Similarity	NPC76478
0.7207	Intermediate Similarity	NPC138830
0.7205	Intermediate Similarity	NPC473006
0.7203	Intermediate Similarity	NPC471513
0.7202	Intermediate Similarity	NPC63152
0.7196	Intermediate Similarity	NPC473562
0.7195	Intermediate Similarity	NPC234933
0.7182	Intermediate Similarity	NPC33256
0.7181	Intermediate Similarity	NPC475133
0.7179	Intermediate Similarity	NPC148124
0.7155	Intermediate Similarity	NPC77777
0.7155	Intermediate Similarity	NPC82056
0.7143	Intermediate Similarity	NPC477397
0.7137	Intermediate Similarity	NPC291173
0.7137	Intermediate Similarity	NPC46259
0.7137	Intermediate Similarity	NPC329830
0.7137	Intermediate Similarity	NPC99724
0.7131	Intermediate Similarity	NPC477395
0.7131	Intermediate Similarity	NPC13249
0.713	Intermediate Similarity	NPC114468
0.713	Intermediate Similarity	NPC67904
0.7124	Intermediate Similarity	NPC223590
0.7124	Intermediate Similarity	NPC246140
0.7124	Intermediate Similarity	NPC288110
0.7124	Intermediate Similarity	NPC195787
0.7123	Intermediate Similarity	NPC473004
0.7123	Intermediate Similarity	NPC226708
0.7119	Intermediate Similarity	NPC115588
0.7106	Intermediate Similarity	NPC106593
0.7104	Intermediate Similarity	NPC477258
0.7103	Intermediate Similarity	NPC476428
0.7103	Intermediate Similarity	NPC329816
0.71	Intermediate Similarity	NPC2905
0.7093	Intermediate Similarity	NPC478075
0.7091	Intermediate Similarity	NPC94499
0.7091	Intermediate Similarity	NPC471825
0.7089	Intermediate Similarity	NPC266994
0.7085	Intermediate Similarity	NPC477396
0.708	Intermediate Similarity	NPC87714
0.7074	Intermediate Similarity	NPC269449
0.7073	Intermediate Similarity	NPC477393
0.7064	Intermediate Similarity	NPC477259
0.7064	Intermediate Similarity	NPC7560
0.7064	Intermediate Similarity	NPC169387
0.7056	Intermediate Similarity	NPC222524
0.7056	Intermediate Similarity	NPC85613
0.7056	Intermediate Similarity	NPC5167
0.7045	Intermediate Similarity	NPC114039
0.7045	Intermediate Similarity	NPC206109
0.704	Intermediate Similarity	NPC83019
0.704	Intermediate Similarity	NPC193906
0.704	Intermediate Similarity	NPC23080
0.704	Intermediate Similarity	NPC100863
0.7039	Intermediate Similarity	NPC473837
0.7034	Intermediate Similarity	NPC71539
0.7034	Intermediate Similarity	NPC250960
0.7029	Intermediate Similarity	NPC74216
0.7026	Intermediate Similarity	NPC55470
0.7021	Intermediate Similarity	NPC140311
0.7018	Intermediate Similarity	NPC212123
0.7018	Intermediate Similarity	NPC308943
0.7013	Intermediate Similarity	NPC119722
0.7004	Intermediate Similarity	NPC473667
0.6996	Remote Similarity	NPC272706
0.6996	Remote Similarity	NPC204580
0.6992	Remote Similarity	NPC469722
0.6991	Remote Similarity	NPC473660
0.6991	Remote Similarity	NPC15987
0.6991	Remote Similarity	NPC474077
0.6991	Remote Similarity	NPC27887
0.6983	Remote Similarity	NPC185031
0.6983	Remote Similarity	NPC30749
0.6982	Remote Similarity	NPC230313
0.6979	Remote Similarity	NPC108826
0.6975	Remote Similarity	NPC21638
0.6974	Remote Similarity	NPC477161
0.6971	Remote Similarity	NPC211215
0.6966	Remote Similarity	NPC475180
0.6957	Remote Similarity	NPC46990
0.6957	Remote Similarity	NPC168250
0.6957	Remote Similarity	NPC477160
0.6955	Remote Similarity	NPC473569
0.6953	Remote Similarity	NPC189661
0.6949	Remote Similarity	NPC472099
0.6947	Remote Similarity	NPC471489
0.6946	Remote Similarity	NPC285254
0.694	Remote Similarity	NPC470481
0.694	Remote Similarity	NPC305542
0.694	Remote Similarity	NPC470482
0.6933	Remote Similarity	NPC241263
0.6927	Remote Similarity	NPC472209
0.6927	Remote Similarity	NPC473007
0.6927	Remote Similarity	NPC478076
0.6909	Remote Similarity	NPC230098
0.6908	Remote Similarity	NPC471303
0.6906	Remote Similarity	NPC469816
0.6906	Remote Similarity	NPC469815
0.6903	Remote Similarity	NPC127178
0.6894	Remote Similarity	NPC126556
0.689	Remote Similarity	NPC329640
0.6886	Remote Similarity	NPC41216

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 NPC476429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	263
0.1-0.2	652
0.2-0.3	955
0.3-0.4	2193
0.4-0.5	3054
0.5-0.6	1698
0.6-0.7	321
0.7-0.8	14
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8	Intermediate Similarity	NPD7708	Approved
0.7942	Intermediate Similarity	NPD7803	Approved
0.7824	Intermediate Similarity	NPD7064	Clinical (unspecified phase)
0.7737	Intermediate Similarity	NPD7956	Approved
0.7737	Intermediate Similarity	NPD7955	Approved
0.7615	Intermediate Similarity	NPD5006	Approved
0.7615	Intermediate Similarity	NPD5005	Approved
0.7564	Intermediate Similarity	NPD6625	Approved
0.7512	Intermediate Similarity	NPD5071	Phase 2
0.7431	Intermediate Similarity	NPD4420	Approved
0.7395	Intermediate Similarity	NPD4846	Phase 2
0.7306	Intermediate Similarity	NPD6621	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD2899	Discontinued
0.719	Intermediate Similarity	NPD7885	Phase 2
0.719	Intermediate Similarity	NPD7886	Phase 2
0.7188	Intermediate Similarity	NPD7497	Discontinued
0.7177	Intermediate Similarity	NPD5242	Approved
0.7162	Intermediate Similarity	NPD6874	Approved
0.7123	Intermediate Similarity	NPD5313	Approved
0.7123	Intermediate Similarity	NPD5312	Approved
0.7067	Intermediate Similarity	NPD956	Clinical (unspecified phase)
0.7064	Intermediate Similarity	NPD6608	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD6386	Approved
0.7024	Intermediate Similarity	NPD6385	Approved
0.7021	Intermediate Similarity	NPD7858	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5353	Approved
0.692	Remote Similarity	NPD7238	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD6723	Discontinued
0.6903	Remote Similarity	NPD4107	Approved
0.69	Remote Similarity	NPD7607	Clinical (unspecified phase)
0.6887	Remote Similarity	NPD5186	Approved
0.6887	Remote Similarity	NPD5183	Approved
0.6884	Remote Similarity	NPD8156	Discontinued
0.6875	Remote Similarity	NPD7223	Discontinued
0.6875	Remote Similarity	NPD7224	Discontinued
0.6867	Remote Similarity	NPD7225	Discontinued
0.6863	Remote Similarity	NPD8461	Discontinued
0.6842	Remote Similarity	NPD5978	Approved
0.6842	Remote Similarity	NPD5977	Approved
0.6837	Remote Similarity	NPD8251	Approved
0.6837	Remote Similarity	NPD8099	Discontinued
0.6837	Remote Similarity	NPD8252	Approved
0.6828	Remote Similarity	NPD7255	Clinical (unspecified phase)
0.6824	Remote Similarity	NPD683	Approved
0.6809	Remote Similarity	NPD7559	Phase 2
0.68	Remote Similarity	NPD5582	Discontinued
0.6798	Remote Similarity	NPD4482	Phase 3
0.6792	Remote Similarity	NPD7278	Phase 2
0.6792	Remote Similarity	NPD7279	Phase 2
0.6781	Remote Similarity	NPD5860	Discontinued
0.6781	Remote Similarity	NPD4997	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8149	Discontinued
0.6778	Remote Similarity	NPD7805	Phase 3
0.6778	Remote Similarity	NPD7907	Approved
0.6776	Remote Similarity	NPD7922	Phase 1
0.6773	Remote Similarity	NPD6021	Clinical (unspecified phase)
0.6773	Remote Similarity	NPD6618	Phase 2
0.6767	Remote Similarity	NPD4859	Phase 1
0.6761	Remote Similarity	NPD7048	Phase 3
0.675	Remote Similarity	NPD6997	Phase 2
0.6736	Remote Similarity	NPD3437	Discontinued
0.6727	Remote Similarity	NPD2968	Approved
0.6727	Remote Similarity	NPD2971	Approved
0.6727	Remote Similarity	NPD7281	Phase 3
0.6727	Remote Similarity	NPD7280	Phase 3
0.6726	Remote Similarity	NPD7667	Clinical (unspecified phase)
0.6722	Remote Similarity	NPD5619	Clinical (unspecified phase)
0.6719	Remote Similarity	NPD8350	Clinical (unspecified phase)
0.6711	Remote Similarity	NPD7810	Phase 3
0.6711	Remote Similarity	NPD7811	Phase 3
0.6696	Remote Similarity	NPD2973	Approved
0.6696	Remote Similarity	NPD2974	Approved
0.6696	Remote Similarity	NPD2975	Approved
0.6695	Remote Similarity	NPD2906	Approved
0.6695	Remote Similarity	NPD2907	Approved
0.6693	Remote Similarity	NPD6525	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD6107	Approved
0.6681	Remote Similarity	NPD4580	Approved
0.6667	Remote Similarity	NPD7186	Phase 3
0.6667	Remote Similarity	NPD4885	Approved
0.6667	Remote Similarity	NPD6654	Clinical (unspecified phase)
0.6654	Remote Similarity	NPD8492	Approved
0.6654	Remote Similarity	NPD7862	Clinical (unspecified phase)
0.6653	Remote Similarity	NPD3912	Discontinued
0.6652	Remote Similarity	NPD5896	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD5742	Approved
0.6651	Remote Similarity	NPD5741	Approved
0.6651	Remote Similarity	NPD5743	Approved
0.6625	Remote Similarity	NPD4111	Phase 1
0.6625	Remote Similarity	NPD4665	Approved
0.6624	Remote Similarity	NPD7571	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD4082	Approved
0.6624	Remote Similarity	NPD8027	Approved
0.6622	Remote Similarity	NPD7090	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD8054	Approved
0.6622	Remote Similarity	NPD8053	Approved
0.6622	Remote Similarity	NPD5525	Clinical (unspecified phase)
0.6611	Remote Similarity	NPD3940	Clinical (unspecified phase)
0.661	Remote Similarity	NPD5676	Approved
0.6609	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD6457	Approved
0.6603	Remote Similarity	NPD4120	Approved
0.6603	Remote Similarity	NPD4121	Phase 3
0.659	Remote Similarity	NPD4481	Phase 3
0.6587	Remote Similarity	NPD3641	Approved
0.6587	Remote Similarity	NPD3639	Approved
0.6587	Remote Similarity	NPD3640	Phase 3
0.6587	Remote Similarity	NPD1483	Discontinued
0.658	Remote Similarity	NPD3450	Approved
0.658	Remote Similarity	NPD2494	Approved
0.658	Remote Similarity	NPD3452	Approved
0.658	Remote Similarity	NPD2493	Approved
0.658	Remote Similarity	NPD6238	Discontinued
0.6579	Remote Similarity	NPD7880	Clinical (unspecified phase)
0.6578	Remote Similarity	NPD7235	Clinical (unspecified phase)
0.6575	Remote Similarity	NPD3050	Clinical (unspecified phase)
0.6574	Remote Similarity	NPD7025	Clinical (unspecified phase)
0.6573	Remote Similarity	NPD6788	Approved
0.6569	Remote Similarity	NPD5025	Approved
0.6567	Remote Similarity	NPD4582	Approved
0.6567	Remote Similarity	NPD5102	Clinical (unspecified phase)
0.6567	Remote Similarity	NPD4583	Approved
0.6558	Remote Similarity	NPD5677	Discontinued
0.6558	Remote Similarity	NPD5494	Approved
0.6552	Remote Similarity	NPD3057	Approved
0.6552	Remote Similarity	NPD7627	Approved
0.6552	Remote Similarity	NPD7626	Approved
0.655	Remote Similarity	NPD4926	Clinical (unspecified phase)
0.654	Remote Similarity	NPD6873	Phase 2
0.6533	Remote Similarity	NPD7291	Discontinued
0.6532	Remote Similarity	NPD7797	Approved
0.6532	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6532	Remote Similarity	NPD7796	Approved
0.653	Remote Similarity	NPD4498	Clinical (unspecified phase)
0.6529	Remote Similarity	NPD3783	Clinical (unspecified phase)
0.6528	Remote Similarity	NPD2821	Approved
0.6524	Remote Similarity	NPD7597	Clinical (unspecified phase)
0.6524	Remote Similarity	NPD4004	Approved
0.6524	Remote Similarity	NPD4002	Approved
0.6516	Remote Similarity	NPD6293	Clinical (unspecified phase)
0.6514	Remote Similarity	NPD6365	Clinical (unspecified phase)
0.6513	Remote Similarity	NPD4492	Approved
0.6513	Remote Similarity	NPD4494	Approved
0.6511	Remote Similarity	NPD7263	Phase 2
0.6509	Remote Similarity	NPD6321	Discontinued
0.6509	Remote Similarity	NPD7298	Approved
0.6508	Remote Similarity	NPD7560	Approved
0.6504	Remote Similarity	NPD5928	Phase 1
0.65	Remote Similarity	NPD7047	Phase 3
0.6498	Remote Similarity	NPD8367	Approved
0.6498	Remote Similarity	NPD8153	Approved
0.6498	Remote Similarity	NPD5914	Approved
0.6498	Remote Similarity	NPD8152	Approved
0.6493	Remote Similarity	NPD1337	Clinical (unspecified phase)
0.6489	Remote Similarity	NPD4084	Clinical (unspecified phase)
0.6488	Remote Similarity	NPD5496	Approved
0.6484	Remote Similarity	NPD8358	Approved
0.6482	Remote Similarity	NPD7417	Discontinued
0.6481	Remote Similarity	NPD3533	Approved
0.6481	Remote Similarity	NPD2972	Approved
0.6481	Remote Similarity	NPD8467	Approved
0.6481	Remote Similarity	NPD8465	Approved
0.6481	Remote Similarity	NPD8466	Approved
0.6477	Remote Similarity	NPD7690	Clinical (unspecified phase)
0.6476	Remote Similarity	NPD2490	Approved
0.6476	Remote Similarity	NPD2488	Approved
0.6473	Remote Similarity	NPD5980	Discovery
0.6473	Remote Similarity	NPD8404	Phase 2
0.6473	Remote Similarity	NPD6851	Approved
0.6473	Remote Similarity	NPD6853	Approved
0.6471	Remote Similarity	NPD6567	Clinical (unspecified phase)
0.6471	Remote Similarity	NPD4493	Discontinued
0.6471	Remote Similarity	NPD5900	Clinical (unspecified phase)
0.6468	Remote Similarity	NPD7174	Clinical (unspecified phase)
0.646	Remote Similarity	NPD5620	Clinical (unspecified phase)
0.6457	Remote Similarity	NPD6716	Phase 1
0.6455	Remote Similarity	NPD5603	Clinical (unspecified phase)
0.6452	Remote Similarity	NPD6199	Discontinued
0.6447	Remote Similarity	NPD7296	Approved
0.6445	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6444	Remote Similarity	NPD7827	Phase 1
0.644	Remote Similarity	NPD7942	Clinical (unspecified phase)
0.644	Remote Similarity	NPD6741	Clinical (unspecified phase)
0.6438	Remote Similarity	NPD7566	Clinical (unspecified phase)
0.6429	Remote Similarity	NPD5726	Clinical (unspecified phase)
0.6426	Remote Similarity	NPD7891	Discontinued
0.6426	Remote Similarity	NPD6228	Discontinued
0.6426	Remote Similarity	NPD6644	Discontinued
0.6425	Remote Similarity	NPD5600	Discontinued
0.6425	Remote Similarity	NPD5521	Clinical (unspecified phase)
0.6423	Remote Similarity	NPD8463	Approved
0.6423	Remote Similarity	NPD7821	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6422	Remote Similarity	NPD3297	Approved
0.6422	Remote Similarity	NPD1880	Phase 3
0.6419	Remote Similarity	NPD5019	Clinical (unspecified phase)
0.6417	Remote Similarity	NPD4455	Discontinued
0.6414	Remote Similarity	NPD6593	Clinical (unspecified phase)
0.6412	Remote Similarity	NPD8091	Phase 3
0.6411	Remote Similarity	NPD4584	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