NPASS Compound

Structure

NPC474905 OpenBabel07101719122D 38 42 0 0 1 0 0 0 0 0999 V2000 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4145 -3.8271 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 9.0023 -3.0181 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4200 -3.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5955 -2.1045 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -3.0000 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 5.1962 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 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 3.4641 0.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 7.0132 -2.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 0.5000 0.0000 C 0 0 3 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 7.6010 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.1962 2.0000 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 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 N 0 0 0 0 0 0 0 0 0 0 0 0 7.0132 -1.1910 0.0000 N 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 -1.7321 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 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 6.0622 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 -0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 3 2 0 0 0 0 2 35 1 0 0 0 0 3 13 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 28 1 0 0 0 0 10 16 1 0 0 0 0 10 19 1 0 0 0 0 11 30 1 0 0 0 0 12 17 2 0 0 0 0 12 36 1 0 0 0 0 13 16 1 0 0 0 0 13 26 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 0 0 0 0 17 25 1 0 0 0 0 18 29 1 0 0 0 0 19 21 1 0 0 0 0 19 28 2 0 0 0 0 20 11 1 6 0 0 0 20 22 1 0 0 0 0 20 37 1 0 0 0 0 21 29 1 0 0 0 0 22 23 1 0 0 0 0 22 31 1 1 0 0 0 23 24 1 0 0 0 0 23 32 1 6 0 0 0 24 27 1 0 0 0 0 24 33 1 1 0 0 0 25 34 2 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 26 38 1 6 0 0 0 27 37 1 0 0 0 0 27 38 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	528.21
Volume:	512.78
LogP:	1.641
LogD:	1.494
LogS:	-3.212
# Rotatable Bonds:	8
TPSA:	163.06
# H-Bond Aceptor:	11
# H-Bond Donor:	5
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.255
Synthetic Accessibility Score:	4.917
Fsp3:	0.481
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:	-6.084
MDCK Permeability:	2.058604331978131e-05
Pgp-inhibitor:	0.014
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.566
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	0.946

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.581
Plasma Protein Binding (PPB):	83.8447494506836%
Volume Distribution (VD):	1.141
Pgp-substrate:	23.46361541748047%

ADMET: Metabolism

CYP1A2-inhibitor:	0.068
CYP1A2-substrate:	0.166
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.179
CYP2C9-inhibitor:	0.03
CYP2C9-substrate:	0.152
CYP2D6-inhibitor:	0.035
CYP2D6-substrate:	0.332
CYP3A4-inhibitor:	0.119
CYP3A4-substrate:	0.418

ADMET: Excretion

Clearance (CL):	1.483
Half-life (T1/2):	0.58

ADMET: Toxicity

hERG Blockers:	0.412
Human Hepatotoxicity (H-HT):	0.26
Drug-inuced Liver Injury (DILI):	0.16
AMES Toxicity:	0.25
Rat Oral Acute Toxicity:	0.537
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.083
Carcinogencity:	0.916
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.957

Download Data

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

Natural Product: NPC474905

Natural Product ID:	NPC474905
*Common Name:**	KWPBQSXTICIPDO-JXHODNCLSA-N
IUPAC Name:	n.a.
Synonyms:	3,4-Dehydro-Strictosidine
Standard InCHIKey:	KWPBQSXTICIPDO-JXHODNCLSA-N
Standard InCHI:	InChI=1S/C27H32N2O9/c1-3-13-16(10-19-21-15(8-9-28-19)14-6-4-5-7-18(14)29-21)17(25(34)35-2)12-36-26(13)38-27-24(33)23(32)22(31)20(11-30)37-27/h3-7,12-13,16,20,22-24,26-27,29-33H,1,8-11H2,2H3/t13?,16?,20-,22-,23+,24-,26+,27+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C(C(C2C=C)CC2=NCCc3c2[nH]c2c3cccc2)C(=O)OC)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL487079
PubChem CID:	n.a.
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0002049] Terpene glycosides

*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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	55100.0	nM	PMID[464738]

☑ 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 NPC474905 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	236
0.1-0.2	1135
0.2-0.3	3701
0.3-0.4	12521
0.4-0.5	17934
0.5-0.6	4826
0.6-0.7	1983
0.7-0.8	322
0.8-0.85	21
0.85-0.9	6
0.9-0.95	10
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC476115
0.9282	High Similarity	NPC82070
0.9082	High Similarity	NPC476114
0.905	High Similarity	NPC475271
0.904	High Similarity	NPC52254
0.8614	High Similarity	NPC174788
0.8492	Intermediate Similarity	NPC477548
0.8357	Intermediate Similarity	NPC57453
0.8182	Intermediate Similarity	NPC312870
0.8182	Intermediate Similarity	NPC199851
0.8182	Intermediate Similarity	NPC294909
0.8182	Intermediate Similarity	NPC254240
0.8182	Intermediate Similarity	NPC128265
0.8107	Intermediate Similarity	NPC313640
0.7911	Intermediate Similarity	NPC473800
0.7892	Intermediate Similarity	NPC18661
0.7861	Intermediate Similarity	NPC160127
0.7861	Intermediate Similarity	NPC50997
0.7857	Intermediate Similarity	NPC102338
0.7857	Intermediate Similarity	NPC63199
0.7857	Intermediate Similarity	NPC111602
0.7857	Intermediate Similarity	NPC196251
0.7773	Intermediate Similarity	NPC249428
0.775	Intermediate Similarity	NPC19692
0.775	Intermediate Similarity	NPC220151
0.7731	Intermediate Similarity	NPC472762
0.7716	Intermediate Similarity	NPC325775
0.7716	Intermediate Similarity	NPC328798
0.7714	Intermediate Similarity	NPC234078
0.7714	Intermediate Similarity	NPC221100
0.7677	Intermediate Similarity	NPC46413
0.7677	Intermediate Similarity	NPC175474
0.765	Intermediate Similarity	NPC475424
0.765	Intermediate Similarity	NPC79107
0.7638	Intermediate Similarity	NPC472112
0.76	Intermediate Similarity	NPC127647
0.7573	Intermediate Similarity	NPC476874
0.7562	Intermediate Similarity	NPC472113
0.7562	Intermediate Similarity	NPC55493
0.7561	Intermediate Similarity	NPC313985
0.7561	Intermediate Similarity	NPC49196
0.7561	Intermediate Similarity	NPC81654
0.7561	Intermediate Similarity	NPC249150
0.7561	Intermediate Similarity	NPC195461
0.7561	Intermediate Similarity	NPC79129
0.755	Intermediate Similarity	NPC469470
0.755	Intermediate Similarity	NPC469501
0.7523	Intermediate Similarity	NPC21638
0.7513	Intermediate Similarity	NPC325093
0.7513	Intermediate Similarity	NPC327373
0.7513	Intermediate Similarity	NPC472108
0.7513	Intermediate Similarity	NPC322043
0.7513	Intermediate Similarity	NPC139291
0.7512	Intermediate Similarity	NPC274842
0.7512	Intermediate Similarity	NPC241024
0.7512	Intermediate Similarity	NPC471284
0.75	Intermediate Similarity	NPC235900
0.75	Intermediate Similarity	NPC182814
0.75	Intermediate Similarity	NPC244856
0.7476	Intermediate Similarity	NPC214428
0.7465	Intermediate Similarity	NPC236424
0.7465	Intermediate Similarity	NPC306644
0.7463	Intermediate Similarity	NPC52557
0.7463	Intermediate Similarity	NPC50503
0.7462	Intermediate Similarity	NPC71037
0.7451	Intermediate Similarity	NPC245916
0.7449	Intermediate Similarity	NPC270009
0.7437	Intermediate Similarity	NPC318020
0.7427	Intermediate Similarity	NPC192674
0.7427	Intermediate Similarity	NPC32200
0.7426	Intermediate Similarity	NPC129909
0.7426	Intermediate Similarity	NPC472097
0.7424	Intermediate Similarity	NPC472444
0.7413	Intermediate Similarity	NPC34271
0.7407	Intermediate Similarity	NPC281049
0.7404	Intermediate Similarity	NPC123019
0.7402	Intermediate Similarity	NPC20593
0.74	Intermediate Similarity	NPC235684
0.7385	Intermediate Similarity	NPC2395
0.7383	Intermediate Similarity	NPC229348
0.7381	Intermediate Similarity	NPC238457
0.7381	Intermediate Similarity	NPC277350
0.7376	Intermediate Similarity	NPC314333
0.7366	Intermediate Similarity	NPC472293
0.7366	Intermediate Similarity	NPC231342
0.7363	Intermediate Similarity	NPC119700
0.7361	Intermediate Similarity	NPC312645
0.7361	Intermediate Similarity	NPC96131
0.7358	Intermediate Similarity	NPC284102
0.735	Intermediate Similarity	NPC280290
0.7346	Intermediate Similarity	NPC46225
0.7343	Intermediate Similarity	NPC472297
0.7343	Intermediate Similarity	NPC472296
0.7337	Intermediate Similarity	NPC469358
0.7333	Intermediate Similarity	NPC34508
0.7328	Intermediate Similarity	NPC476516
0.7327	Intermediate Similarity	NPC61435
0.7324	Intermediate Similarity	NPC475165
0.7324	Intermediate Similarity	NPC234999
0.7321	Intermediate Similarity	NPC474192
0.7321	Intermediate Similarity	NPC475720
0.7317	Intermediate Similarity	NPC85066
0.7317	Intermediate Similarity	NPC181502
0.7315	Intermediate Similarity	NPC288349
0.7313	Intermediate Similarity	NPC315555
0.7311	Intermediate Similarity	NPC127677
0.7304	Intermediate Similarity	NPC472292
0.7302	Intermediate Similarity	NPC473547
0.7296	Intermediate Similarity	NPC472586
0.7292	Intermediate Similarity	NPC311276
0.7291	Intermediate Similarity	NPC206967
0.729	Intermediate Similarity	NPC250129
0.7289	Intermediate Similarity	NPC473105
0.7285	Intermediate Similarity	NPC235885
0.7282	Intermediate Similarity	NPC6982
0.7277	Intermediate Similarity	NPC469743
0.7277	Intermediate Similarity	NPC472435
0.7273	Intermediate Similarity	NPC472443
0.7273	Intermediate Similarity	NPC213468
0.7269	Intermediate Similarity	NPC97388
0.7265	Intermediate Similarity	NPC33949
0.7257	Intermediate Similarity	NPC472436
0.7256	Intermediate Similarity	NPC475778
0.7256	Intermediate Similarity	NPC151976
0.725	Intermediate Similarity	NPC472110
0.725	Intermediate Similarity	NPC472109
0.7249	Intermediate Similarity	NPC471458
0.7249	Intermediate Similarity	NPC470507
0.7244	Intermediate Similarity	NPC89987
0.7235	Intermediate Similarity	NPC152768
0.7235	Intermediate Similarity	NPC148183
0.7232	Intermediate Similarity	NPC471634
0.7232	Intermediate Similarity	NPC473806
0.7228	Intermediate Similarity	NPC311858
0.7222	Intermediate Similarity	NPC89508
0.7222	Intermediate Similarity	NPC28848
0.7222	Intermediate Similarity	NPC14325
0.7222	Intermediate Similarity	NPC472291
0.7214	Intermediate Similarity	NPC258480
0.7214	Intermediate Similarity	NPC165201
0.7212	Intermediate Similarity	NPC102008
0.7206	Intermediate Similarity	NPC329858
0.7204	Intermediate Similarity	NPC98715
0.7202	Intermediate Similarity	NPC40779
0.72	Intermediate Similarity	NPC282033
0.7194	Intermediate Similarity	NPC470498
0.7192	Intermediate Similarity	NPC472323
0.719	Intermediate Similarity	NPC300183
0.7186	Intermediate Similarity	NPC219336
0.7184	Intermediate Similarity	NPC269886
0.7184	Intermediate Similarity	NPC472295
0.7184	Intermediate Similarity	NPC472210
0.7184	Intermediate Similarity	NPC247735
0.7184	Intermediate Similarity	NPC81802
0.7183	Intermediate Similarity	NPC225821
0.7182	Intermediate Similarity	NPC61813
0.7176	Intermediate Similarity	NPC111732
0.7156	Intermediate Similarity	NPC204491
0.7156	Intermediate Similarity	NPC74969
0.7156	Intermediate Similarity	NPC193761
0.715	Intermediate Similarity	NPC258062
0.715	Intermediate Similarity	NPC469896
0.7143	Intermediate Similarity	NPC57690
0.7143	Intermediate Similarity	NPC476514
0.7143	Intermediate Similarity	NPC475151
0.7143	Intermediate Similarity	NPC66210
0.7136	Intermediate Similarity	NPC217372
0.7136	Intermediate Similarity	NPC15573
0.7136	Intermediate Similarity	NPC183662
0.713	Intermediate Similarity	NPC475816
0.713	Intermediate Similarity	NPC141428
0.7129	Intermediate Similarity	NPC470003
0.7129	Intermediate Similarity	NPC149708
0.7121	Intermediate Similarity	NPC189812
0.7121	Intermediate Similarity	NPC329688
0.712	Intermediate Similarity	NPC285469
0.7116	Intermediate Similarity	NPC478158
0.7114	Intermediate Similarity	NPC192270
0.711	Intermediate Similarity	NPC477979
0.711	Intermediate Similarity	NPC478157
0.7103	Intermediate Similarity	NPC323927
0.7103	Intermediate Similarity	NPC244741
0.7098	Intermediate Similarity	NPC473320
0.7098	Intermediate Similarity	NPC267926
0.7097	Intermediate Similarity	NPC87856
0.7097	Intermediate Similarity	NPC292517
0.7097	Intermediate Similarity	NPC207020
0.7092	Intermediate Similarity	NPC78020
0.7092	Intermediate Similarity	NPC317430
0.7092	Intermediate Similarity	NPC154293
0.7085	Intermediate Similarity	NPC266192
0.7085	Intermediate Similarity	NPC472122
0.7085	Intermediate Similarity	NPC267885
0.7085	Intermediate Similarity	NPC24594
0.7083	Intermediate Similarity	NPC469762
0.7083	Intermediate Similarity	NPC191489
0.7077	Intermediate Similarity	NPC470508
0.7075	Intermediate Similarity	NPC162730
0.7075	Intermediate Similarity	NPC474116
0.7071	Intermediate Similarity	NPC472123

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 NPC474905 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	162
0.1-0.2	442
0.2-0.3	634
0.3-0.4	1457
0.4-0.5	3171
0.5-0.6	2599
0.6-0.7	622
0.7-0.8	61
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8182	Intermediate Similarity	NPD4500	Approved
0.8182	Intermediate Similarity	NPD4501	Approved
0.7689	Intermediate Similarity	NPD8325	Phase 3
0.7689	Intermediate Similarity	NPD8326	Phase 3
0.7689	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7598	Intermediate Similarity	NPD6248	Phase 2
0.7598	Intermediate Similarity	NPD6249	Phase 2
0.7586	Intermediate Similarity	NPD5003	Discontinued
0.7561	Intermediate Similarity	NPD4600	Approved
0.7561	Intermediate Similarity	NPD4601	Approved
0.7511	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7441	Intermediate Similarity	NPD4506	Discontinued
0.7427	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7426	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.7424	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7406	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7376	Intermediate Similarity	NPD4499	Approved
0.7371	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5487	Phase 1
0.734	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7336	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.733	Intermediate Similarity	NPD6206	Phase 1
0.7327	Intermediate Similarity	NPD4334	Discontinued
0.7323	Intermediate Similarity	NPD5897	Approved
0.7323	Intermediate Similarity	NPD5898	Approved
0.7323	Intermediate Similarity	NPD5899	Approved
0.7299	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7299	Intermediate Similarity	NPD7957	Phase 1
0.7299	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7295	Intermediate Similarity	NPD6261	Phase 3
0.7291	Intermediate Similarity	NPD2564	Approved
0.7291	Intermediate Similarity	NPD2565	Phase 2
0.7286	Intermediate Similarity	NPD6176	Phase 1
0.725	Intermediate Similarity	NPD2092	Phase 2
0.725	Intermediate Similarity	NPD2095	Phase 2
0.725	Intermediate Similarity	NPD2094	Phase 2
0.7245	Intermediate Similarity	NPD6182	Approved
0.7245	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7245	Intermediate Similarity	NPD43	Approved
0.723	Intermediate Similarity	NPD2509	Approved
0.723	Intermediate Similarity	NPD2510	Approved
0.723	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.723	Intermediate Similarity	NPD8423	Phase 2
0.723	Intermediate Similarity	NPD8399	Phase 1
0.7228	Intermediate Similarity	NPD5444	Phase 1
0.7225	Intermediate Similarity	NPD6479	Discontinued
0.7222	Intermediate Similarity	NPD3794	Approved
0.7222	Intermediate Similarity	NPD3795	Approved
0.7214	Intermediate Similarity	NPD2096	Phase 2
0.7214	Intermediate Similarity	NPD2091	Phase 2
0.7212	Intermediate Similarity	NPD53	Approved
0.7212	Intermediate Similarity	NPD7778	Approved
0.7212	Intermediate Similarity	NPD7777	Approved
0.7189	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD3393	Approved
0.7156	Intermediate Similarity	NPD3389	Approved
0.7156	Intermediate Similarity	NPD3394	Approved
0.7136	Intermediate Similarity	NPD4315	Phase 2
0.7136	Intermediate Similarity	NPD6770	Approved
0.713	Intermediate Similarity	NPD7470	Discontinued
0.7123	Intermediate Similarity	NPD8072	Approved
0.7123	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.711	Intermediate Similarity	NPD4897	Phase 2
0.7092	Intermediate Similarity	NPD2844	Phase 3
0.7085	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD7708	Approved
0.708	Intermediate Similarity	NPD7589	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7233	Approved
0.7073	Intermediate Similarity	NPD7234	Approved
0.7056	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.705	Intermediate Similarity	NPD6641	Approved
0.705	Intermediate Similarity	NPD6642	Approved
0.7042	Intermediate Similarity	NPD7956	Approved
0.7042	Intermediate Similarity	NPD7955	Approved
0.7037	Intermediate Similarity	NPD6529	Discontinued
0.7035	Intermediate Similarity	NPD482	Approved
0.7028	Intermediate Similarity	NPD7727	Phase 2
0.7014	Intermediate Similarity	NPD7878	Phase 2
0.7014	Intermediate Similarity	NPD5632	Approved
0.7009	Intermediate Similarity	NPD5901	Discontinued
0.6995	Remote Similarity	NPD8073	Approved
0.6986	Remote Similarity	NPD4602	Approved
0.6979	Remote Similarity	NPD8468	Phase 2
0.6967	Remote Similarity	NPD7803	Approved
0.6963	Remote Similarity	NPD3777	Phase 3
0.6963	Remote Similarity	NPD2920	Discontinued
0.6959	Remote Similarity	NPD5834	Phase 3
0.6959	Remote Similarity	NPD5835	Phase 3
0.6951	Remote Similarity	NPD3280	Approved
0.693	Remote Similarity	NPD8282	Approved
0.693	Remote Similarity	NPD8283	Approved
0.693	Remote Similarity	NPD56	Approved
0.6927	Remote Similarity	NPD5075	Discontinued
0.692	Remote Similarity	NPD5506	Approved
0.692	Remote Similarity	NPD5507	Approved
0.6915	Remote Similarity	NPD5104	Approved
0.6912	Remote Similarity	NPD5596	Phase 2
0.6904	Remote Similarity	NPD2915	Discontinued
0.6898	Remote Similarity	NPD3003	Approved
0.6872	Remote Similarity	NPD5512	Phase 3
0.687	Remote Similarity	NPD4885	Approved
0.6864	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD8374	Phase 3
0.6854	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6852	Remote Similarity	NPD8115	Approved
0.6852	Remote Similarity	NPD8114	Approved
0.6849	Remote Similarity	NPD5072	Discontinued
0.6849	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.6847	Remote Similarity	NPD4079	Approved
0.6847	Remote Similarity	NPD4076	Approved
0.6847	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6822	Remote Similarity	NPD5427	Suspended
0.6818	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD750	Phase 2
0.6814	Remote Similarity	NPD5473	Discontinued
0.6814	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.681	Remote Similarity	NPD8329	Phase 3
0.6808	Remote Similarity	NPD7946	Pre-registration
0.6802	Remote Similarity	NPD5902	Approved
0.6802	Remote Similarity	NPD5903	Approved
0.68	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD3505	Approved
0.6798	Remote Similarity	NPD2144	Approved
0.6798	Remote Similarity	NPD3506	Approved
0.6797	Remote Similarity	NPD7796	Approved
0.6797	Remote Similarity	NPD7797	Approved
0.6796	Remote Similarity	NPD3436	Approved
0.6792	Remote Similarity	NPD6550	Discontinued
0.6791	Remote Similarity	NPD7817	Phase 1
0.6789	Remote Similarity	NPD7562	Approved
0.6784	Remote Similarity	NPD7548	Discontinued
0.678	Remote Similarity	NPD3038	Discontinued
0.6776	Remote Similarity	NPD1768	Approved
0.6771	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6767	Remote Similarity	NPD7558	Phase 2
0.6747	Remote Similarity	NPD8363	Approved
0.6747	Remote Similarity	NPD8364	Approved
0.6746	Remote Similarity	NPD1534	Approved
0.6745	Remote Similarity	NPD7944	Discontinued
0.6744	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6743	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6742	Remote Similarity	NPD5067	Phase 2
0.6742	Remote Similarity	NPD5066	Phase 2
0.6742	Remote Similarity	NPD5416	Discontinued
0.674	Remote Similarity	NPD6824	Clinical (unspecified phase)
0.6736	Remote Similarity	NPD4463	Approved
0.6736	Remote Similarity	NPD4462	Approved
0.6735	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6735	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6726	Remote Similarity	NPD6242	Discontinued
0.6719	Remote Similarity	NPD8429	Approved
0.6719	Remote Similarity	NPD8427	Approved
0.6719	Remote Similarity	NPD8465	Approved
0.6719	Remote Similarity	NPD8466	Approved
0.6719	Remote Similarity	NPD8428	Approved
0.6719	Remote Similarity	NPD8467	Approved
0.6718	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD6178	Phase 3
0.6712	Remote Similarity	NPD7573	Discontinued
0.6709	Remote Similarity	NPD6517	Phase 3
0.67	Remote Similarity	NPD5065	Approved
0.67	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3435	Discontinued
0.6699	Remote Similarity	NPD4948	Discontinued
0.6697	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6693	Remote Similarity	NPD8365	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5913	Phase 3
0.6682	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5501	Discontinued
0.6667	Remote Similarity	NPD7780	Approved
0.6667	Remote Similarity	NPD484	Approved
0.6667	Remote Similarity	NPD7781	Approved
0.6667	Remote Similarity	NPD5475	Discontinued
0.6667	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6652	Remote Similarity	NPD8289	Discontinued
0.6652	Remote Similarity	NPD7707	Approved
0.6652	Remote Similarity	NPD5293	Phase 2
0.6652	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD4987	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD6669	Phase 2
0.665	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6649	Remote Similarity	NPD3833	Phase 3
0.6649	Remote Similarity	NPD3835	Phase 3
0.6638	Remote Similarity	NPD7716	Approved
0.6638	Remote Similarity	NPD3006	Discontinued
0.6638	Remote Similarity	NPD7853	Phase 2
0.6638	Remote Similarity	NPD7717	Approved
0.6637	Remote Similarity	NPD7395	Discontinued
0.6637	Remote Similarity	NPD7069	Discontinued
0.6636	Remote Similarity	NPD7903	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD7061	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD5429	Discontinued
0.6635	Remote Similarity	NPD6281	Approved
0.6634	Remote Similarity	NPD1325	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