NPASS Compound

Structure

CID302449 OpenBabel06191716112D 35 40 0 0 1 0 0 0 0 0999 V2000 5.9652 -0.4325 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4041 -1.1928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7659 -0.7538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.4041 -2.0708 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8082 -1.3794 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3925 -3.6077 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5933 -3.3935 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8999 -4.9917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1833 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7658 -3.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7659 -2.5097 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3327 -4.1645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0492 -5.4056 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3330 -4.9917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7658 -3.3371 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5932 -4.9919 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8074 -4.1927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6165 -4.5780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1834 -3.7506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7659 -2.5097 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0492 -4.5782 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.6165 -3.7506 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8999 -3.3369 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3327 -2.5097 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.5262 -1.1928 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5262 -2.0708 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0493 -3.7508 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3327 -3.3371 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0493 -2.0960 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7658 -4.9919 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.4325 -3.3171 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9651 -2.8311 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6356 -1.3794 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2684 -2.3211 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.5444 -2.7803 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 5 33 1 0 0 0 0 6 7 1 0 0 0 0 6 17 1 0 0 0 0 7 17 1 0 0 0 0 8 9 2 0 0 0 0 8 18 1 0 0 0 0 9 19 1 0 0 0 0 10 11 1 0 0 0 0 10 27 1 0 0 0 0 12 13 1 0 0 0 0 13 30 1 0 0 0 0 14 18 1 0 0 0 0 14 21 1 0 0 0 0 15 20 1 0 0 0 0 15 27 1 0 0 0 0 16 17 1 0 0 0 0 16 30 1 0 0 0 0 18 22 2 0 0 0 0 19 23 2 0 0 0 0 19 31 1 0 0 0 0 20 26 1 0 0 0 0 20 29 1 1 0 0 0 21 27 1 6 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 28 1 0 0 0 0 23 34 1 0 0 0 0 24 28 1 1 0 0 0 24 29 1 0 0 0 0 24 34 1 0 0 0 0 25 26 1 0 0 0 0 26 4 1 6 0 0 0 26 32 1 0 0 0 0 27 28 1 6 0 0 0 28 12 1 6 0 0 0 29 11 1 1 0 0 0 29 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	467.3
Volume:	488.493
LogP:	5.102
LogD:	3.987
LogS:	-4.523
# Rotatable Bonds:	5
TPSA:	62.16
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	8
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.687
Synthetic Accessibility Score:	6.456
Fsp3:	0.793
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.274
MDCK Permeability:	1.37093020384782e-05
Pgp-inhibitor:	0.025
Pgp-substrate:	0.838
Human Intestinal Absorption (HIA):	0.02
20% Bioavailability (F20%):	0.021
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.537
Plasma Protein Binding (PPB):	94.58271026611328%
Volume Distribution (VD):	4.335
Pgp-substrate:	6.00640344619751%

ADMET: Metabolism

CYP1A2-inhibitor:	0.03
CYP1A2-substrate:	0.516
CYP2C19-inhibitor:	0.071
CYP2C19-substrate:	0.855
CYP2C9-inhibitor:	0.102
CYP2C9-substrate:	0.242
CYP2D6-inhibitor:	0.943
CYP2D6-substrate:	0.897
CYP3A4-inhibitor:	0.744
CYP3A4-substrate:	0.889

ADMET: Excretion

Clearance (CL):	11.631
Half-life (T1/2):	0.232

ADMET: Toxicity

hERG Blockers:	0.972
Human Hepatotoxicity (H-HT):	0.554
Drug-inuced Liver Injury (DILI):	0.045
AMES Toxicity:	0.019
Rat Oral Acute Toxicity:	0.894
Maximum Recommended Daily Dose:	0.915
Skin Sensitization:	0.48
Carcinogencity:	0.569
Eye Corrosion:	0.003
Eye Irritation:	0.009
Respiratory Toxicity:	0.948

Download Data

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

Natural Product: NPC302449

Natural Product ID:	NPC302449
*Common Name:**	UAIXRPCCYXNJMQ-RZIPZOSSSA-N
IUPAC Name:	n.a.
Synonyms:	Buprenorphine HCl; CL-112302; NIH-8805; RX-6029-M; UM-952
Standard InCHIKey:	UAIXRPCCYXNJMQ-RZIPZOSSSA-N
Standard InCHI:	InChI=1S/C29H41NO4.ClH/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28;/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3;1H/t20-,21-,24-,26+,27-,28+,29-;/m1./s1
SMILES:	CC(C)(C)[C@](C)([C@H]1C[C@]23CC[C@@]1([C@H]1[C@]43CCN(CC3CC3)[C@@H]2Cc2ccc(c(c42)O1)O)OC)O.Cl
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1200401
PubChem CID:	3033050 45265653
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0002448] Benzenoids [CHEMONTID:0000025] Phenanthrenes 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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	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	3

Activity Type	# Activity
Individual Protein	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT145	Individual Protein	Mu opioid receptor	Homo sapiens	IC50	=	1.7	nM	PMID[11585443]
NPT272	Individual Protein	Kappa opioid receptor	Homo sapiens	IC50	=	1.2	nM	PMID[11585443]
NPT271	Individual Protein	Delta opioid receptor	Homo sapiens	IC50	=	0.9	nM	PMID[11585443]

☑ 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 NPC302449 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	386
0.1-0.2	1500
0.2-0.3	4487
0.3-0.4	9934
0.4-0.5	9538
0.5-0.6	11611
0.6-0.7	4648
0.7-0.8	560
0.8-0.85	22
0.85-0.9	9
0.9-0.95	0
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9939	High Similarity	NPC305847
0.9096	High Similarity	NPC124657
0.8675	High Similarity	NPC180756
0.8675	High Similarity	NPC323443
0.8563	High Similarity	NPC329969
0.8418	Intermediate Similarity	NPC99179
0.8382	Intermediate Similarity	NPC474931
0.8382	Intermediate Similarity	NPC12053
0.8382	Intermediate Similarity	NPC158376
0.8382	Intermediate Similarity	NPC306555
0.8382	Intermediate Similarity	NPC145832
0.8382	Intermediate Similarity	NPC117188
0.8382	Intermediate Similarity	NPC205421
0.8382	Intermediate Similarity	NPC81218
0.8289	Intermediate Similarity	NPC254045
0.8289	Intermediate Similarity	NPC64576
0.8289	Intermediate Similarity	NPC151470
0.8289	Intermediate Similarity	NPC201055
0.8266	Intermediate Similarity	NPC96603
0.8266	Intermediate Similarity	NPC212794
0.8266	Intermediate Similarity	NPC78222
0.8266	Intermediate Similarity	NPC477563
0.8266	Intermediate Similarity	NPC13504
0.8266	Intermediate Similarity	NPC253043
0.8266	Intermediate Similarity	NPC196447
0.8266	Intermediate Similarity	NPC136508
0.8266	Intermediate Similarity	NPC306843
0.8258	Intermediate Similarity	NPC320223
0.8258	Intermediate Similarity	NPC114364
0.8208	Intermediate Similarity	NPC324144
0.8208	Intermediate Similarity	NPC1229
0.8198	Intermediate Similarity	NPC205167
0.8198	Intermediate Similarity	NPC249274
0.8172	Intermediate Similarity	NPC66909
0.8146	Intermediate Similarity	NPC229166
0.8146	Intermediate Similarity	NPC199465
0.8146	Intermediate Similarity	NPC128560
0.8136	Intermediate Similarity	NPC239775
0.8108	Intermediate Similarity	NPC478093
0.8092	Intermediate Similarity	NPC27410
0.8092	Intermediate Similarity	NPC18402
0.8092	Intermediate Similarity	NPC166014
0.809	Intermediate Similarity	NPC192135
0.809	Intermediate Similarity	NPC66341
0.809	Intermediate Similarity	NPC477020
0.8079	Intermediate Similarity	NPC118274
0.8079	Intermediate Similarity	NPC168753
0.8066	Intermediate Similarity	NPC115906
0.8065	Intermediate Similarity	NPC30182
0.8065	Intermediate Similarity	NPC473589
0.8065	Intermediate Similarity	NPC478092
0.8065	Intermediate Similarity	NPC478091
0.8057	Intermediate Similarity	NPC3375
0.8057	Intermediate Similarity	NPC255607
0.8053	Intermediate Similarity	NPC97086
0.8033	Intermediate Similarity	NPC214629
0.8023	Intermediate Similarity	NPC83198
0.8023	Intermediate Similarity	NPC147091
0.8023	Intermediate Similarity	NPC204908
0.8022	Intermediate Similarity	NPC248642
0.7989	Intermediate Similarity	NPC4304
0.7989	Intermediate Similarity	NPC232386
0.7989	Intermediate Similarity	NPC190783
0.7989	Intermediate Similarity	NPC152680
0.7978	Intermediate Similarity	NPC135772
0.7978	Intermediate Similarity	NPC26240
0.7978	Intermediate Similarity	NPC156576
0.7978	Intermediate Similarity	NPC69712
0.7978	Intermediate Similarity	NPC477562
0.7977	Intermediate Similarity	NPC315707
0.7977	Intermediate Similarity	NPC78359
0.7977	Intermediate Similarity	NPC40389
0.7977	Intermediate Similarity	NPC65490
0.7977	Intermediate Similarity	NPC476572
0.7977	Intermediate Similarity	NPC148014
0.7967	Intermediate Similarity	NPC286119
0.7958	Intermediate Similarity	NPC232533
0.7958	Intermediate Similarity	NPC67346
0.7957	Intermediate Similarity	NPC475754
0.7956	Intermediate Similarity	NPC118633
0.7956	Intermediate Similarity	NPC294790
0.7956	Intermediate Similarity	NPC148693
0.7946	Intermediate Similarity	NPC275680
0.7946	Intermediate Similarity	NPC22115
0.7923	Intermediate Similarity	NPC8836
0.7923	Intermediate Similarity	NPC54654
0.7923	Intermediate Similarity	NPC181796
0.7923	Intermediate Similarity	NPC229373
0.7923	Intermediate Similarity	NPC217748
0.7923	Intermediate Similarity	NPC182052
0.7923	Intermediate Similarity	NPC271013
0.7923	Intermediate Similarity	NPC290582
0.7923	Intermediate Similarity	NPC42663
0.7923	Intermediate Similarity	NPC185639
0.7923	Intermediate Similarity	NPC104196
0.7923	Intermediate Similarity	NPC7715
0.7923	Intermediate Similarity	NPC222661
0.7923	Intermediate Similarity	NPC279228
0.7923	Intermediate Similarity	NPC116284
0.7923	Intermediate Similarity	NPC239824
0.7923	Intermediate Similarity	NPC258657
0.7923	Intermediate Similarity	NPC49075
0.7923	Intermediate Similarity	NPC311973
0.7923	Intermediate Similarity	NPC30779
0.7923	Intermediate Similarity	NPC90998
0.7923	Intermediate Similarity	NPC223690
0.7923	Intermediate Similarity	NPC290005
0.7923	Intermediate Similarity	NPC285931
0.7923	Intermediate Similarity	NPC328155
0.7923	Intermediate Similarity	NPC15414
0.7923	Intermediate Similarity	NPC251735
0.7912	Intermediate Similarity	NPC126284
0.7912	Intermediate Similarity	NPC474507
0.791	Intermediate Similarity	NPC13916
0.791	Intermediate Similarity	NPC264850
0.7903	Intermediate Similarity	NPC206900
0.7892	Intermediate Similarity	NPC212237
0.7892	Intermediate Similarity	NPC116465
0.7886	Intermediate Similarity	NPC226428
0.788	Intermediate Similarity	NPC274716
0.788	Intermediate Similarity	NPC254441
0.788	Intermediate Similarity	NPC167116
0.7874	Intermediate Similarity	NPC129603
0.7869	Intermediate Similarity	NPC476574
0.7869	Intermediate Similarity	NPC298339
0.7869	Intermediate Similarity	NPC312918
0.7869	Intermediate Similarity	NPC155442
0.7869	Intermediate Similarity	NPC477561
0.7865	Intermediate Similarity	NPC298979
0.7865	Intermediate Similarity	NPC243483
0.7865	Intermediate Similarity	NPC247389
0.7865	Intermediate Similarity	NPC140577
0.7865	Intermediate Similarity	NPC43069
0.7861	Intermediate Similarity	NPC325871
0.7861	Intermediate Similarity	NPC295691
0.7861	Intermediate Similarity	NPC469817
0.7861	Intermediate Similarity	NPC172765
0.7861	Intermediate Similarity	NPC278799
0.7861	Intermediate Similarity	NPC189266
0.7861	Intermediate Similarity	NPC110416
0.7861	Intermediate Similarity	NPC2413
0.7861	Intermediate Similarity	NPC193949
0.7861	Intermediate Similarity	NPC39701
0.7861	Intermediate Similarity	NPC276588
0.7861	Intermediate Similarity	NPC207757
0.7861	Intermediate Similarity	NPC54379
0.7861	Intermediate Similarity	NPC204828
0.7861	Intermediate Similarity	NPC249797
0.7861	Intermediate Similarity	NPC99659
0.7861	Intermediate Similarity	NPC5238
0.7861	Intermediate Similarity	NPC127674
0.7861	Intermediate Similarity	NPC184026
0.7853	Intermediate Similarity	NPC24465
0.7841	Intermediate Similarity	NPC60186
0.7838	Intermediate Similarity	NPC302245
0.7838	Intermediate Similarity	NPC95426
0.7838	Intermediate Similarity	NPC16357
0.7826	Intermediate Similarity	NPC233718
0.7824	Intermediate Similarity	NPC476571
0.7824	Intermediate Similarity	NPC135538
0.7824	Intermediate Similarity	NPC24233
0.7824	Intermediate Similarity	NPC147390
0.7824	Intermediate Similarity	NPC428
0.7824	Intermediate Similarity	NPC246587
0.7819	Intermediate Similarity	NPC24260
0.7814	Intermediate Similarity	NPC32154
0.7809	Intermediate Similarity	NPC268503
0.7809	Intermediate Similarity	NPC35627
0.7809	Intermediate Similarity	NPC24264
0.7809	Intermediate Similarity	NPC42549
0.7809	Intermediate Similarity	NPC476573
0.7809	Intermediate Similarity	NPC317272
0.7809	Intermediate Similarity	NPC219341
0.7809	Intermediate Similarity	NPC250846
0.7809	Intermediate Similarity	NPC476432
0.7809	Intermediate Similarity	NPC240841
0.7809	Intermediate Similarity	NPC256012
0.7809	Intermediate Similarity	NPC81247
0.7807	Intermediate Similarity	NPC82763
0.7802	Intermediate Similarity	NPC148709
0.7802	Intermediate Similarity	NPC476577
0.7802	Intermediate Similarity	NPC173416
0.7797	Intermediate Similarity	NPC218614
0.7796	Intermediate Similarity	NPC214116
0.7796	Intermediate Similarity	NPC65312
0.7796	Intermediate Similarity	NPC139783
0.779	Intermediate Similarity	NPC2314
0.7778	Intermediate Similarity	NPC477565
0.7778	Intermediate Similarity	NPC103379
0.7765	Intermediate Similarity	NPC210140
0.7765	Intermediate Similarity	NPC191376
0.7765	Intermediate Similarity	NPC179825
0.7765	Intermediate Similarity	NPC181653
0.7765	Intermediate Similarity	NPC321505
0.7765	Intermediate Similarity	NPC190332
0.7765	Intermediate Similarity	NPC252960
0.7765	Intermediate Similarity	NPC150879
0.776	Intermediate Similarity	NPC15919
0.7754	Intermediate Similarity	NPC476576
0.7754	Intermediate Similarity	NPC186546

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 NPC302449 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	224
0.1-0.2	756
0.2-0.3	1239
0.3-0.4	2809
0.4-0.5	2250
0.5-0.6	1329
0.6-0.7	455
0.7-0.8	45
0.8-0.85	23
0.85-0.9	12
0.9-0.95	3
0.95-1	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7309	Approved
0.9939	High Similarity	NPD7312	Approved
0.9939	High Similarity	NPD7310	Approved
0.9939	High Similarity	NPD7311	Approved
0.9939	High Similarity	NPD7313	Approved
0.9235	High Similarity	NPD4577	Approved
0.9235	High Similarity	NPD4578	Approved
0.9217	High Similarity	NPD2489	Approved
0.9217	High Similarity	NPD27	Approved
0.9157	High Similarity	NPD2970	Approved
0.9157	High Similarity	NPD2969	Approved
0.9023	High Similarity	NPD7906	Approved
0.8982	High Similarity	NPD3051	Approved
0.8966	High Similarity	NPD4663	Approved
0.8655	High Similarity	NPD4481	Phase 3
0.8548	High Similarity	NPD4583	Approved
0.8548	High Similarity	NPD4582	Approved
0.8495	Intermediate Similarity	NPD4002	Approved
0.8495	Intermediate Similarity	NPD4004	Approved
0.8398	Intermediate Similarity	NPD2488	Approved
0.8398	Intermediate Similarity	NPD2490	Approved
0.8387	Intermediate Similarity	NPD2493	Approved
0.8387	Intermediate Similarity	NPD2494	Approved
0.8333	Intermediate Similarity	NPD4580	Approved
0.8289	Intermediate Similarity	NPD3452	Approved
0.8289	Intermediate Similarity	NPD3450	Approved
0.8205	Intermediate Similarity	NPD7047	Phase 3
0.8172	Intermediate Similarity	NPD2974	Approved
0.8172	Intermediate Similarity	NPD2975	Approved
0.8172	Intermediate Similarity	NPD2973	Approved
0.8114	Intermediate Similarity	NPD6071	Discontinued
0.8066	Intermediate Similarity	NPD2971	Approved
0.8066	Intermediate Similarity	NPD2968	Approved
0.799	Intermediate Similarity	NPD4111	Phase 1
0.7977	Intermediate Similarity	NPD2560	Approved
0.7977	Intermediate Similarity	NPD2563	Approved
0.7969	Intermediate Similarity	NPD4040	Phase 1
0.7958	Intermediate Similarity	NPD3057	Approved
0.7958	Intermediate Similarity	NPD2491	Approved
0.7923	Intermediate Similarity	NPD8054	Approved
0.7923	Intermediate Similarity	NPD8053	Approved
0.7871	Intermediate Similarity	NPD6997	Phase 2
0.787	Intermediate Similarity	NPD1754	Clinical (unspecified phase)
0.7869	Intermediate Similarity	NPD3534	Clinical (unspecified phase)
0.7865	Intermediate Similarity	NPD3448	Approved
0.7865	Intermediate Similarity	NPD2972	Approved
0.7865	Intermediate Similarity	NPD3533	Approved
0.7822	Intermediate Similarity	NPD7907	Approved
0.7811	Intermediate Similarity	NPD4665	Approved
0.7784	Intermediate Similarity	NPD7831	Phase 2
0.7784	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD7833	Phase 2
0.7727	Intermediate Similarity	NPD5676	Approved
0.7668	Intermediate Similarity	NPD4107	Approved
0.7659	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7624	Intermediate Similarity	NPD2898	Approved
0.76	Intermediate Similarity	NPD4773	Phase 2
0.76	Intermediate Similarity	NPD4772	Phase 2
0.7596	Intermediate Similarity	NPD8156	Discontinued
0.7594	Intermediate Similarity	NPD7048	Phase 3
0.7588	Intermediate Similarity	NPD5241	Discontinued
0.7545	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7541	Intermediate Similarity	NPD8252	Approved
0.7541	Intermediate Similarity	NPD8099	Discontinued
0.7541	Intermediate Similarity	NPD8251	Approved
0.7538	Intermediate Similarity	NPD4482	Phase 3
0.7514	Intermediate Similarity	NPD5772	Approved
0.7514	Intermediate Similarity	NPD5773	Approved
0.7457	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7457	Intermediate Similarity	NPD4584	Approved
0.7416	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7412	Intermediate Similarity	NPD4664	Clinical (unspecified phase)
0.741	Intermediate Similarity	NPD3110	Approved
0.741	Intermediate Similarity	NPD3109	Approved
0.7401	Intermediate Similarity	NPD6072	Discontinued
0.7399	Intermediate Similarity	NPD2421	Approved
0.7399	Intermediate Similarity	NPD2420	Approved
0.7368	Intermediate Similarity	NPD5177	Phase 3
0.7337	Intermediate Similarity	NPD1753	Discontinued
0.7318	Intermediate Similarity	NPD2978	Approved
0.7318	Intermediate Similarity	NPD2977	Approved
0.7312	Intermediate Similarity	NPD42	Phase 2
0.7312	Intermediate Similarity	NPD6042	Phase 2
0.7286	Intermediate Similarity	NPD7497	Discontinued
0.7282	Intermediate Similarity	NPD5980	Discovery
0.7267	Intermediate Similarity	NPD4236	Phase 3
0.7267	Intermediate Similarity	NPD4237	Approved
0.7251	Intermediate Similarity	NPD4721	Approved
0.7251	Intermediate Similarity	NPD4726	Approved
0.7251	Intermediate Similarity	NPD4725	Approved
0.7249	Intermediate Similarity	NPD7549	Discontinued
0.7202	Intermediate Similarity	NPD2238	Phase 2
0.7194	Intermediate Similarity	NPD7667	Clinical (unspecified phase)
0.7175	Intermediate Similarity	NPD2122	Discontinued
0.7173	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2606	Approved
0.7169	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD2605	Approved
0.7167	Intermediate Similarity	NPD7298	Approved
0.7159	Intermediate Similarity	NPD7447	Phase 1
0.7151	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6667	Approved
0.7143	Intermediate Similarity	NPD7124	Phase 2
0.7143	Intermediate Similarity	NPD6666	Approved
0.7135	Intermediate Similarity	NPD4210	Discontinued
0.7135	Intermediate Similarity	NPD4010	Discontinued
0.7126	Intermediate Similarity	NPD5155	Approved
0.7126	Intermediate Similarity	NPD5156	Approved
0.712	Intermediate Similarity	NPD4666	Phase 3
0.7119	Intermediate Similarity	NPD3647	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD7037	Approved
0.7108	Intermediate Similarity	NPD3636	Approved
0.7108	Intermediate Similarity	NPD3637	Approved
0.7108	Intermediate Similarity	NPD3635	Approved
0.7102	Intermediate Similarity	NPD7213	Phase 3
0.7102	Intermediate Similarity	NPD7212	Phase 2
0.7086	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD3692	Discontinued
0.7086	Intermediate Similarity	NPD2677	Approved
0.7085	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD6030	Approved
0.7079	Intermediate Similarity	NPD6031	Approved
0.7079	Intermediate Similarity	NPD4727	Phase 1
0.7076	Intermediate Similarity	NPD6896	Approved
0.7076	Intermediate Similarity	NPD6895	Approved
0.7069	Intermediate Similarity	NPD3060	Approved
0.7066	Intermediate Similarity	NPD3595	Approved
0.7066	Intermediate Similarity	NPD3594	Approved
0.7065	Intermediate Similarity	NPD5709	Phase 3
0.7045	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7045	Intermediate Similarity	NPD2422	Clinical (unspecified phase)
0.7029	Intermediate Similarity	NPD5754	Discontinued
0.7029	Intermediate Similarity	NPD6331	Phase 2
0.7027	Intermediate Similarity	NPD7201	Clinical (unspecified phase)
0.7024	Intermediate Similarity	NPD2669	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD6090	Discontinued
0.7022	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7022	Intermediate Similarity	NPD7526	Approved
0.7022	Intermediate Similarity	NPD52	Approved
0.7011	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD4017	Approved
0.6991	Remote Similarity	NPD6503	Clinical (unspecified phase)
0.6982	Remote Similarity	NPD5718	Phase 2
0.6971	Remote Similarity	NPD6674	Discontinued
0.6971	Remote Similarity	NPD4162	Approved
0.6966	Remote Similarity	NPD7020	Approved
0.6966	Remote Similarity	NPD7019	Approved
0.6957	Remote Similarity	NPD4581	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD6788	Approved
0.6954	Remote Similarity	NPD1375	Discontinued
0.6944	Remote Similarity	NPD3686	Approved
0.6944	Remote Similarity	NPD3687	Approved
0.6935	Remote Similarity	NPD3365	Discontinued
0.6932	Remote Similarity	NPD7466	Approved
0.6932	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD8051	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD4257	Approved
0.6914	Remote Similarity	NPD4256	Phase 2
0.6913	Remote Similarity	NPD7169	Suspended
0.6906	Remote Similarity	NPD4005	Discontinued
0.6901	Remote Similarity	NPD1612	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.6901	Remote Similarity	NPD1613	Approved
0.6901	Remote Similarity	NPD3620	Phase 2
0.6898	Remote Similarity	NPD6107	Approved
0.6897	Remote Similarity	NPD2161	Phase 2
0.6891	Remote Similarity	NPD8453	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD3639	Approved
0.6889	Remote Similarity	NPD3641	Approved
0.6889	Remote Similarity	NPD3640	Phase 3
0.6888	Remote Similarity	NPD7243	Clinical (unspecified phase)
0.6885	Remote Similarity	NPD5722	Discontinued
0.6879	Remote Similarity	NPD2200	Suspended
0.6872	Remote Similarity	NPD4123	Phase 3
0.6869	Remote Similarity	NPD7296	Approved
0.6866	Remote Similarity	NPD4420	Approved
0.6854	Remote Similarity	NPD3122	Phase 3
0.6842	Remote Similarity	NPD7827	Phase 1
0.6833	Remote Similarity	NPD5261	Clinical (unspecified phase)
0.6832	Remote Similarity	NPD8095	Phase 1
0.6825	Remote Similarity	NPD6687	Approved
0.6825	Remote Similarity	NPD6688	Approved
0.6821	Remote Similarity	NPD823	Approved
0.6821	Remote Similarity	NPD817	Approved
0.6816	Remote Similarity	NPD1774	Approved
0.6807	Remote Similarity	NPD2233	Approved
0.6807	Remote Similarity	NPD2232	Approved
0.6807	Remote Similarity	NPD2230	Approved
0.6804	Remote Similarity	NPD4419	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD7501	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5307	Clinical (unspecified phase)
0.6796	Remote Similarity	NPD5976	Discontinued
0.6784	Remote Similarity	NPD6812	Clinical (unspecified phase)
0.6784	Remote Similarity	NPD6410	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD6111	Discontinued
0.6778	Remote Similarity	NPD3645	Discontinued
0.6776	Remote Similarity	NPD4678	Approved
0.6776	Remote Similarity	NPD4675	Approved
0.6772	Remote Similarity	NPD7315	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