NPASS Compound

Structure

CID264153 OpenBabel06191716062D 36 39 0 0 1 0 0 0 0 0999 V2000 -3.0000 2.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 0.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1340 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5981 0.7679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1340 -0.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7321 -0.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5468 2.4704 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4641 1.2679 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 0.7679 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -6.5686 2.2625 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -0.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0000 -0.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8660 -2.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0000 -1.7321 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.3776 0.8612 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.8660 -0.2321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0000 -1.7321 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5000 0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.8255 2.9316 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.8660 -3.2321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.5856 -0.1169 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.0468 1.6044 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 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 1 13 2 0 0 0 0 4 7 1 0 0 0 0 4 13 1 0 0 0 0 5 6 1 0 0 0 0 5 14 2 0 0 0 0 6 15 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 19 1 0 0 0 0 9 25 1 0 0 0 0 10 27 1 0 0 0 0 11 16 1 0 0 0 0 11 34 1 0 0 0 0 12 26 1 0 0 0 0 12 35 1 0 0 0 0 13 15 1 0 0 0 0 14 16 1 0 0 0 0 14 23 1 0 0 0 0 15 25 1 6 0 0 0 16 28 1 1 0 0 0 17 10 1 6 0 0 0 17 20 1 0 0 0 0 17 36 1 0 0 0 0 18 25 1 6 0 0 0 18 26 1 0 0 0 0 19 26 1 6 0 0 0 19 29 1 0 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 22 1 0 0 0 0 21 31 1 6 0 0 0 22 24 1 0 0 0 0 22 32 1 1 0 0 0 23 33 2 0 0 0 0 23 34 1 0 0 0 0 24 35 1 6 0 0 0 24 36 1 0 0 0 0 25 2 1 6 0 0 0 26 3 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	512.26
Volume:	504.019
LogP:	0.911
LogD:	0.217
LogS:	-2.467
# Rotatable Bonds:	6
TPSA:	166.14
# H-Bond Aceptor:	10
# H-Bond Donor:	6
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.204
Synthetic Accessibility Score:	5.374
Fsp3:	0.808
Lipinski Rule-of-5:	Rejected
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:	-5.79
MDCK Permeability:	8.204236655728891e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.55
Human Intestinal Absorption (HIA):	0.843
20% Bioavailability (F20%):	0.574
30% Bioavailability (F30%):	0.938

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.121
Plasma Protein Binding (PPB):	30.123653411865234%
Volume Distribution (VD):	0.338
Pgp-substrate:	48.60758590698242%

ADMET: Metabolism

CYP1A2-inhibitor:	0.011
CYP1A2-substrate:	0.066
CYP2C19-inhibitor:	0.004
CYP2C19-substrate:	0.124
CYP2C9-inhibitor:	0.001
CYP2C9-substrate:	0.032
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.1
CYP3A4-inhibitor:	0.07
CYP3A4-substrate:	0.046

ADMET: Excretion

Clearance (CL):	1.256
Half-life (T1/2):	0.772

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.048
Drug-inuced Liver Injury (DILI):	0.08
AMES Toxicity:	0.619
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.924
Skin Sensitization:	0.125
Carcinogencity:	0.022
Eye Corrosion:	0.003
Eye Irritation:	0.021
Respiratory Toxicity:	0.081

Download Data

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

Natural Product: NPC264153

Natural Product ID:	NPC264153
*Common Name:**	Andrographiside
IUPAC Name:	(3E,4S)-3-[2-[(1R,4aS,5R,6R,8aS)-6-hydroxy-5,8a-dimethyl-2-methylidene-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]ethylidene]-4-hydroxyoxolan-2-one
Synonyms:	Andrographiside
Standard InCHIKey:	VUEPOIYXKZTLMD-ANZZXSATSA-N
Standard InCHI:	InChI=1S/C26H40O10/c1-13-4-7-18-25(2,15(13)6-5-14-16(28)11-34-23(14)33)9-8-19(29)26(18,3)12-35-24-22(32)21(31)20(30)17(10-27)36-24/h5,15-22,24,27-32H,1,4,6-12H2,2-3H3/b14-5+/t15-,16-,17-,18+,19-,20-,21+,22-,24-,25+,26+/m1/s1
SMILES:	OC[C@H]1O[C@@H](OC[C@]2(C)[C@H](O)CC[C@@]3([C@@H]2CCC(=C)[C@H]3C/C=C/2[C@H](O)COC2=O)C)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL519275
PubChem CID:	44593583
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0002207] O-glycosyl compounds

*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
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	root	n.a.	PMID[15894448]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	aerial parts	purchased in Juhuacun herbal market, Kunming, Yunnan Province, China	2002-Oct	PMID[16562826]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18357994]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21598983]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	leaf	n.a.	PMID[22026410]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8377022]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3578	Andrographis paniculata	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3578	Andrographis paniculata	Species	Acanthaceae	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
GI50	1

Activity Type	# Activity
Cell Line	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell Line	HL-60	Homo sapiens	GI50	=	28830.0	nM	PMID[470946]

☑ 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 NPC264153 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	226
0.1-0.2	1353
0.2-0.3	4004
0.3-0.4	7019
0.4-0.5	11981
0.5-0.6	8261
0.6-0.7	5929
0.7-0.8	3378
0.8-0.85	483
0.85-0.9	59
0.9-0.95	3
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9009	High Similarity	NPC474483
0.8857	High Similarity	NPC121423
0.8796	High Similarity	NPC219900
0.8796	High Similarity	NPC177524
0.8796	High Similarity	NPC392
0.8772	High Similarity	NPC476150
0.8772	High Similarity	NPC476127
0.875	High Similarity	NPC473154
0.875	High Similarity	NPC124512
0.875	High Similarity	NPC278386
0.875	High Similarity	NPC159763
0.8716	High Similarity	NPC206618
0.8696	High Similarity	NPC170084
0.8696	High Similarity	NPC476204
0.8684	High Similarity	NPC470914
0.8679	High Similarity	NPC201191
0.8673	High Similarity	NPC473968
0.8654	High Similarity	NPC73911
0.8649	High Similarity	NPC328074
0.8649	High Similarity	NPC317460
0.8649	High Similarity	NPC321272
0.8649	High Similarity	NPC470025
0.8636	High Similarity	NPC235014
0.8624	High Similarity	NPC135015
0.8624	High Similarity	NPC48548
0.8624	High Similarity	NPC128795
0.8624	High Similarity	NPC217921
0.8624	High Similarity	NPC38948
0.8611	High Similarity	NPC239961
0.8611	High Similarity	NPC218158
0.8609	High Similarity	NPC281840
0.8609	High Similarity	NPC48692
0.8585	High Similarity	NPC198992
0.8571	High Similarity	NPC473159
0.8571	High Similarity	NPC470027
0.8559	High Similarity	NPC17791
0.8545	High Similarity	NPC40728
0.8545	High Similarity	NPC316974
0.8532	High Similarity	NPC88013
0.8532	High Similarity	NPC293512
0.8532	High Similarity	NPC125423
0.8522	High Similarity	NPC122971
0.8512	High Similarity	NPC319719
0.8512	High Similarity	NPC322904
0.8512	High Similarity	NPC478152
0.8512	High Similarity	NPC475177
0.8512	High Similarity	NPC233223
0.8512	High Similarity	NPC183816
0.8512	High Similarity	NPC196874
0.8512	High Similarity	NPC324933
0.8512	High Similarity	NPC231240
0.8512	High Similarity	NPC478150
0.8512	High Similarity	NPC473679
0.8512	High Similarity	NPC475444
0.8512	High Similarity	NPC478153
0.85	High Similarity	NPC476966
0.85	High Similarity	NPC473593
0.8482	Intermediate Similarity	NPC269530
0.8475	Intermediate Similarity	NPC470922
0.8468	Intermediate Similarity	NPC316708
0.8455	Intermediate Similarity	NPC470024
0.8455	Intermediate Similarity	NPC311223
0.8448	Intermediate Similarity	NPC470312
0.8443	Intermediate Similarity	NPC316915
0.8443	Intermediate Similarity	NPC478151
0.844	Intermediate Similarity	NPC82251
0.8435	Intermediate Similarity	NPC234522
0.8435	Intermediate Similarity	NPC473828
0.8435	Intermediate Similarity	NPC473617
0.843	Intermediate Similarity	NPC173435
0.843	Intermediate Similarity	NPC478155
0.843	Intermediate Similarity	NPC262796
0.843	Intermediate Similarity	NPC134914
0.843	Intermediate Similarity	NPC311178
0.843	Intermediate Similarity	NPC300655
0.843	Intermediate Similarity	NPC45346
0.843	Intermediate Similarity	NPC478064
0.843	Intermediate Similarity	NPC25998
0.843	Intermediate Similarity	NPC329993
0.843	Intermediate Similarity	NPC301639
0.843	Intermediate Similarity	NPC264566
0.843	Intermediate Similarity	NPC478065
0.843	Intermediate Similarity	NPC475167
0.843	Intermediate Similarity	NPC475377
0.843	Intermediate Similarity	NPC476074
0.843	Intermediate Similarity	NPC43589
0.843	Intermediate Similarity	NPC172374
0.843	Intermediate Similarity	NPC222951
0.8426	Intermediate Similarity	NPC127933
0.8426	Intermediate Similarity	NPC7644
0.8426	Intermediate Similarity	NPC475889
0.8426	Intermediate Similarity	NPC7613
0.8426	Intermediate Similarity	NPC281378
0.8421	Intermediate Similarity	NPC207637
0.8407	Intermediate Similarity	NPC474410
0.8407	Intermediate Similarity	NPC293658
0.8407	Intermediate Similarity	NPC157441
0.8396	Intermediate Similarity	NPC477928
0.8393	Intermediate Similarity	NPC470026
0.8365	Intermediate Similarity	NPC57117
0.8364	Intermediate Similarity	NPC109376
0.8364	Intermediate Similarity	NPC472390
0.8362	Intermediate Similarity	NPC477071
0.8362	Intermediate Similarity	NPC475775
0.8362	Intermediate Similarity	NPC476529
0.8361	Intermediate Similarity	NPC478154
0.8349	Intermediate Similarity	NPC470768
0.8349	Intermediate Similarity	NPC201880
0.8349	Intermediate Similarity	NPC470321
0.8349	Intermediate Similarity	NPC471937
0.8349	Intermediate Similarity	NPC264867
0.8349	Intermediate Similarity	NPC473207
0.8349	Intermediate Similarity	NPC81567
0.8348	Intermediate Similarity	NPC203862
0.8347	Intermediate Similarity	NPC477077
0.8347	Intermediate Similarity	NPC477076
0.8347	Intermediate Similarity	NPC477079
0.8347	Intermediate Similarity	NPC470913
0.8333	Intermediate Similarity	NPC181145
0.8333	Intermediate Similarity	NPC472274
0.8333	Intermediate Similarity	NPC298841
0.8333	Intermediate Similarity	NPC150463
0.8333	Intermediate Similarity	NPC238397
0.8333	Intermediate Similarity	NPC42399
0.8333	Intermediate Similarity	NPC470516
0.8333	Intermediate Similarity	NPC471363
0.8333	Intermediate Similarity	NPC470780
0.8333	Intermediate Similarity	NPC472815
0.8319	Intermediate Similarity	NPC194951
0.8319	Intermediate Similarity	NPC12046
0.8319	Intermediate Similarity	NPC318135
0.8304	Intermediate Similarity	NPC83005
0.8304	Intermediate Similarity	NPC177047
0.8304	Intermediate Similarity	NPC46407
0.8304	Intermediate Similarity	NPC119550
0.8304	Intermediate Similarity	NPC476766
0.8291	Intermediate Similarity	NPC107338
0.8291	Intermediate Similarity	NPC109607
0.8288	Intermediate Similarity	NPC224660
0.8288	Intermediate Similarity	NPC181994
0.8279	Intermediate Similarity	NPC476852
0.8279	Intermediate Similarity	NPC477197
0.8276	Intermediate Similarity	NPC470515
0.8273	Intermediate Similarity	NPC172867
0.8264	Intermediate Similarity	NPC477193
0.8264	Intermediate Similarity	NPC311534
0.8264	Intermediate Similarity	NPC475281
0.8264	Intermediate Similarity	NPC472268
0.8264	Intermediate Similarity	NPC473620
0.8264	Intermediate Similarity	NPC477194
0.8264	Intermediate Similarity	NPC45606
0.8264	Intermediate Similarity	NPC477192
0.8264	Intermediate Similarity	NPC220838
0.8264	Intermediate Similarity	NPC477191
0.8264	Intermediate Similarity	NPC472270
0.8264	Intermediate Similarity	NPC23020
0.8264	Intermediate Similarity	NPC472269
0.8264	Intermediate Similarity	NPC477078
0.8264	Intermediate Similarity	NPC329923
0.8264	Intermediate Similarity	NPC245094
0.8264	Intermediate Similarity	NPC476859
0.8264	Intermediate Similarity	NPC112492
0.8264	Intermediate Similarity	NPC477075
0.8261	Intermediate Similarity	NPC310341
0.8261	Intermediate Similarity	NPC193382
0.8261	Intermediate Similarity	NPC44170
0.8261	Intermediate Similarity	NPC199428
0.8261	Intermediate Similarity	NPC471816
0.8261	Intermediate Similarity	NPC268954
0.8261	Intermediate Similarity	NPC99620
0.8261	Intermediate Similarity	NPC5311
0.8261	Intermediate Similarity	NPC470075
0.8257	Intermediate Similarity	NPC120009
0.8257	Intermediate Similarity	NPC134270
0.8257	Intermediate Similarity	NPC471938
0.8246	Intermediate Similarity	NPC75167
0.8246	Intermediate Similarity	NPC311592
0.8241	Intermediate Similarity	NPC11974
0.8241	Intermediate Similarity	NPC477717
0.8235	Intermediate Similarity	NPC67251
0.822	Intermediate Similarity	NPC202051
0.822	Intermediate Similarity	NPC129434
0.8214	Intermediate Similarity	NPC476759
0.8214	Intermediate Similarity	NPC31522
0.8214	Intermediate Similarity	NPC257853
0.8211	Intermediate Similarity	NPC473918
0.8211	Intermediate Similarity	NPC30279
0.8211	Intermediate Similarity	NPC46823
0.8211	Intermediate Similarity	NPC192765
0.8211	Intermediate Similarity	NPC178264
0.8211	Intermediate Similarity	NPC71391
0.8211	Intermediate Similarity	NPC277212
0.8208	Intermediate Similarity	NPC90583
0.8205	Intermediate Similarity	NPC470915
0.8205	Intermediate Similarity	NPC44899
0.8205	Intermediate Similarity	NPC470517
0.8205	Intermediate Similarity	NPC470911
0.8205	Intermediate Similarity	NPC29639
0.8205	Intermediate Similarity	NPC304260
0.8205	Intermediate Similarity	NPC5883

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 NPC264153 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	196
0.1-0.2	1498
0.2-0.3	3693
0.3-0.4	2429
0.4-0.5	777
0.5-0.6	331
0.6-0.7	183
0.7-0.8	30
0.8-0.85	11
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8796	High Similarity	NPD6686	Approved
0.875	High Similarity	NPD4225	Approved
0.812	Intermediate Similarity	NPD7327	Approved
0.812	Intermediate Similarity	NPD7328	Approved
0.8067	Intermediate Similarity	NPD8033	Approved
0.8051	Intermediate Similarity	NPD7516	Approved
0.8049	Intermediate Similarity	NPD7319	Approved
0.7983	Intermediate Similarity	NPD8294	Approved
0.7983	Intermediate Similarity	NPD8377	Approved
0.7951	Intermediate Similarity	NPD7507	Approved
0.7917	Intermediate Similarity	NPD7503	Approved
0.7917	Intermediate Similarity	NPD8296	Approved
0.7917	Intermediate Similarity	NPD8379	Approved
0.7917	Intermediate Similarity	NPD8378	Approved
0.7917	Intermediate Similarity	NPD8335	Approved
0.7917	Intermediate Similarity	NPD8380	Approved
0.7818	Intermediate Similarity	NPD7640	Approved
0.7818	Intermediate Similarity	NPD7639	Approved
0.7787	Intermediate Similarity	NPD8328	Phase 3
0.7769	Intermediate Similarity	NPD8513	Phase 3
0.7769	Intermediate Similarity	NPD8515	Approved
0.7769	Intermediate Similarity	NPD8517	Approved
0.7769	Intermediate Similarity	NPD8516	Approved
0.7731	Intermediate Similarity	NPD7115	Discovery
0.7727	Intermediate Similarity	NPD7638	Approved
0.7586	Intermediate Similarity	NPD8132	Clinical (unspecified phase)
0.7583	Intermediate Similarity	NPD8295	Clinical (unspecified phase)
0.7568	Intermediate Similarity	NPD8029	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD6412	Phase 2
0.7479	Intermediate Similarity	NPD8133	Approved
0.7434	Intermediate Similarity	NPD5344	Discontinued
0.7419	Intermediate Similarity	NPD6370	Approved
0.7402	Intermediate Similarity	NPD7736	Approved
0.7323	Intermediate Similarity	NPD8293	Discontinued
0.7311	Intermediate Similarity	NPD8413	Clinical (unspecified phase)
0.7302	Intermediate Similarity	NPD7492	Approved
0.7288	Intermediate Similarity	NPD4061	Clinical (unspecified phase)
0.7258	Intermediate Similarity	NPD6054	Approved
0.7248	Intermediate Similarity	NPD6698	Approved
0.7248	Intermediate Similarity	NPD46	Approved
0.7244	Intermediate Similarity	NPD6616	Approved
0.7227	Intermediate Similarity	NPD6371	Approved
0.7227	Intermediate Similarity	NPD5955	Clinical (unspecified phase)
0.7217	Intermediate Similarity	NPD7632	Discontinued
0.7203	Intermediate Similarity	NPD5345	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7078	Approved
0.7188	Intermediate Similarity	NPD8074	Phase 3
0.712	Intermediate Similarity	NPD6319	Approved
0.712	Intermediate Similarity	NPD6059	Approved
0.7119	Intermediate Similarity	NPD7899	Clinical (unspecified phase)
0.7091	Intermediate Similarity	NPD7838	Discovery
0.7063	Intermediate Similarity	NPD6016	Approved
0.7063	Intermediate Similarity	NPD6015	Approved
0.7043	Intermediate Similarity	NPD6648	Approved
0.7027	Intermediate Similarity	NPD7637	Suspended
0.7009	Intermediate Similarity	NPD6400	Clinical (unspecified phase)
0.7008	Intermediate Similarity	NPD5988	Approved
0.6975	Remote Similarity	NPD5954	Clinical (unspecified phase)
0.6967	Remote Similarity	NPD6882	Approved
0.688	Remote Similarity	NPD6009	Approved
0.6829	Remote Similarity	NPD8297	Approved
0.6822	Remote Similarity	NPD6067	Discontinued
0.6774	Remote Similarity	NPD4632	Approved
0.6748	Remote Similarity	NPD6649	Approved
0.6748	Remote Similarity	NPD6650	Approved
0.6726	Remote Similarity	NPD7983	Approved
0.6724	Remote Similarity	NPD7902	Approved
0.6721	Remote Similarity	NPD6373	Approved
0.6721	Remote Similarity	NPD6372	Approved
0.6696	Remote Similarity	NPD1698	Clinical (unspecified phase)
0.6692	Remote Similarity	NPD7829	Approved
0.6692	Remote Similarity	NPD7830	Approved
0.6667	Remote Similarity	NPD4752	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD6399	Phase 3
0.6667	Remote Similarity	NPD5778	Approved
0.6667	Remote Similarity	NPD5779	Approved
0.6667	Remote Similarity	NPD6921	Approved
0.6639	Remote Similarity	NPD6881	Approved
0.6639	Remote Similarity	NPD6899	Approved
0.6637	Remote Similarity	NPD5785	Approved
0.6617	Remote Similarity	NPD6033	Approved
0.6612	Remote Similarity	NPD7128	Approved
0.6612	Remote Similarity	NPD6402	Approved
0.6612	Remote Similarity	NPD5739	Approved
0.6612	Remote Similarity	NPD6008	Approved
0.6612	Remote Similarity	NPD6675	Approved
0.6609	Remote Similarity	NPD7748	Approved
0.6594	Remote Similarity	NPD7966	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD7515	Phase 2
0.6579	Remote Similarity	NPD6411	Approved
0.6565	Remote Similarity	NPD7642	Approved
0.6557	Remote Similarity	NPD5697	Approved
0.6532	Remote Similarity	NPD6883	Approved
0.6532	Remote Similarity	NPD4634	Approved
0.6532	Remote Similarity	NPD7290	Approved
0.6532	Remote Similarity	NPD7102	Approved
0.6528	Remote Similarity	NPD7625	Phase 1
0.6518	Remote Similarity	NPD7524	Approved
0.6504	Remote Similarity	NPD7320	Approved
0.6486	Remote Similarity	NPD1694	Approved
0.648	Remote Similarity	NPD6869	Approved
0.648	Remote Similarity	NPD6617	Approved
0.648	Remote Similarity	NPD6847	Approved
0.648	Remote Similarity	NPD8130	Phase 1
0.6471	Remote Similarity	NPD7260	Phase 2
0.6466	Remote Similarity	NPD8451	Approved
0.6466	Remote Similarity	NPD7900	Approved
0.6466	Remote Similarity	NPD7901	Clinical (unspecified phase)
0.6466	Remote Similarity	NPD5282	Discontinued
0.6452	Remote Similarity	NPD6012	Approved
0.6452	Remote Similarity	NPD6013	Approved
0.6452	Remote Similarity	NPD6014	Approved
0.6439	Remote Similarity	NPD7604	Phase 2
0.6429	Remote Similarity	NPD3618	Phase 1
0.6429	Remote Similarity	NPD6053	Discontinued
0.6423	Remote Similarity	NPD5701	Approved
0.6418	Remote Similarity	NPD8448	Approved
0.6412	Remote Similarity	NPD5983	Phase 2
0.6404	Remote Similarity	NPD6101	Approved
0.6404	Remote Similarity	NPD5764	Clinical (unspecified phase)
0.6397	Remote Similarity	NPD8392	Approved
0.6397	Remote Similarity	NPD8391	Approved
0.6397	Remote Similarity	NPD8390	Approved
0.6396	Remote Similarity	NPD7338	Clinical (unspecified phase)
0.6391	Remote Similarity	NPD8340	Approved
0.6391	Remote Similarity	NPD8342	Approved
0.6391	Remote Similarity	NPD8341	Approved
0.6391	Remote Similarity	NPD8299	Approved
0.6371	Remote Similarity	NPD6011	Approved
0.6364	Remote Similarity	NPD5211	Phase 2
0.6356	Remote Similarity	NPD7839	Suspended
0.6343	Remote Similarity	NPD6336	Discontinued
0.6308	Remote Similarity	NPD7641	Discontinued
0.6306	Remote Similarity	NPD6695	Phase 3
0.6306	Remote Similarity	NPD3669	Approved
0.6306	Remote Similarity	NPD3670	Clinical (unspecified phase)
0.6304	Remote Similarity	NPD6845	Suspended
0.6303	Remote Similarity	NPD6083	Phase 2
0.6303	Remote Similarity	NPD6084	Phase 2
0.6293	Remote Similarity	NPD8034	Phase 2
0.6293	Remote Similarity	NPD6079	Approved
0.6293	Remote Similarity	NPD8035	Phase 2
0.6288	Remote Similarity	NPD8444	Approved
0.6277	Remote Similarity	NPD5956	Approved
0.6261	Remote Similarity	NPD5328	Approved
0.626	Remote Similarity	NPD5141	Approved
0.626	Remote Similarity	NPD8170	Clinical (unspecified phase)
0.6239	Remote Similarity	NPD8171	Discontinued
0.6228	Remote Similarity	NPD4250	Approved
0.6228	Remote Similarity	NPD4251	Approved
0.622	Remote Similarity	NPD6401	Clinical (unspecified phase)
0.6211	Remote Similarity	NPD7799	Discontinued
0.6198	Remote Similarity	NPD4696	Approved
0.6198	Remote Similarity	NPD5285	Approved
0.6198	Remote Similarity	NPD5286	Approved
0.6195	Remote Similarity	NPD5363	Approved
0.6187	Remote Similarity	NPD8338	Approved
0.6182	Remote Similarity	NPD7525	Registered
0.617	Remote Similarity	NPD8387	Clinical (unspecified phase)
0.6167	Remote Similarity	NPD4755	Approved
0.6159	Remote Similarity	NPD6914	Discontinued
0.6154	Remote Similarity	NPD6274	Approved
0.614	Remote Similarity	NPD5330	Approved
0.614	Remote Similarity	NPD7334	Approved
0.614	Remote Similarity	NPD3574	Clinical (unspecified phase)
0.614	Remote Similarity	NPD6409	Approved
0.614	Remote Similarity	NPD7146	Approved
0.614	Remote Similarity	NPD7521	Approved
0.614	Remote Similarity	NPD4249	Approved
0.614	Remote Similarity	NPD6684	Approved
0.6136	Remote Similarity	NPD7100	Approved
0.6136	Remote Similarity	NPD7101	Approved
0.6134	Remote Similarity	NPD6356	Clinical (unspecified phase)
0.6131	Remote Similarity	NPD8337	Approved
0.6131	Remote Similarity	NPD8336	Approved
0.6121	Remote Similarity	NPD6051	Approved
0.6119	Remote Similarity	NPD8080	Discontinued
0.6116	Remote Similarity	NPD5696	Approved
0.6107	Remote Similarity	NPD8137	Clinical (unspecified phase)
0.6106	Remote Similarity	NPD4786	Approved
0.6102	Remote Similarity	NPD4202	Approved
0.6098	Remote Similarity	NPD4633	Approved
0.6098	Remote Similarity	NPD5226	Approved
0.6098	Remote Similarity	NPD5225	Approved
0.6098	Remote Similarity	NPD5224	Approved
0.6096	Remote Similarity	NPD7266	Discontinued
0.6091	Remote Similarity	NPD6929	Approved
0.6091	Remote Similarity	NPD7645	Phase 2
0.6087	Remote Similarity	NPD7750	Discontinued
0.6087	Remote Similarity	NPD3573	Approved
0.6083	Remote Similarity	NPD4697	Phase 3
0.6083	Remote Similarity	NPD5222	Approved
0.6083	Remote Similarity	NPD5221	Approved
0.6083	Remote Similarity	NPD5220	Clinical (unspecified phase)
0.6071	Remote Similarity	NPD3667	Approved
0.6071	Remote Similarity	NPD8449	Approved
0.6066	Remote Similarity	NPD4700	Approved
0.6061	Remote Similarity	NPD6335	Approved
0.6053	Remote Similarity	NPD1733	Clinical (unspecified phase)
0.6053	Remote Similarity	NPD6082	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