NPASS Compound

Structure

NPC476115 OpenBabel07101719252D 37 41 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 -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 2 2 0 0 0 0 2 12 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 6 1 0 0 0 0 5 13 2 0 0 0 0 6 17 2 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 27 1 0 0 0 0 9 15 1 0 0 0 0 9 18 1 0 0 0 0 10 29 1 0 0 0 0 11 16 2 0 0 0 0 11 35 1 0 0 0 0 12 15 1 0 0 0 0 12 25 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 20 2 0 0 0 0 15 16 1 0 0 0 0 16 24 1 0 0 0 0 17 28 1 0 0 0 0 18 20 1 0 0 0 0 18 27 2 0 0 0 0 19 10 1 6 0 0 0 19 21 1 0 0 0 0 19 36 1 0 0 0 0 20 28 1 0 0 0 0 21 22 1 0 0 0 0 21 30 1 1 0 0 0 22 23 1 0 0 0 0 22 31 1 6 0 0 0 23 26 1 0 0 0 0 23 32 1 1 0 0 0 24 33 2 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 25 37 1 6 0 0 0 26 36 1 0 0 0 0 26 37 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	514.2
Volume:	495.484
LogP:	1.223
LogD:	0.762
LogS:	-2.541
# Rotatable Bonds:	7
TPSA:	174.06
# H-Bond Aceptor:	11
# H-Bond Donor:	6
# Rings:	5
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.287
Synthetic Accessibility Score:	4.93
Fsp3:	0.462
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:	-6.411
MDCK Permeability:	1.410314052918693e-05
Pgp-inhibitor:	0.001
Pgp-substrate:	0.006
Human Intestinal Absorption (HIA):	0.771
20% Bioavailability (F20%):	0.007
30% Bioavailability (F30%):	0.917

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.373
Plasma Protein Binding (PPB):	79.87686920166016%
Volume Distribution (VD):	0.744
Pgp-substrate:	28.26656150817871%

ADMET: Metabolism

CYP1A2-inhibitor:	0.054
CYP1A2-substrate:	0.037
CYP2C19-inhibitor:	0.025
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.017
CYP2C9-substrate:	0.082
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.141
CYP3A4-inhibitor:	0.01
CYP3A4-substrate:	0.146

ADMET: Excretion

Clearance (CL):	1.12
Half-life (T1/2):	0.712

ADMET: Toxicity

hERG Blockers:	0.222
Human Hepatotoxicity (H-HT):	0.226
Drug-inuced Liver Injury (DILI):	0.434
AMES Toxicity:	0.07
Rat Oral Acute Toxicity:	0.69
Maximum Recommended Daily Dose:	0.904
Skin Sensitization:	0.048
Carcinogencity:	0.905
Eye Corrosion:	0.003
Eye Irritation:	0.01
Respiratory Toxicity:	0.956

Download Data

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

Natural Product: NPC476115

Natural Product ID:	NPC476115
*Common Name:**	QNVNXPBFKQJAIB-SZXRKYFWSA-N
IUPAC Name:	n.a.
Synonyms:	3,4-Dehydro-Strictosidinic Acid
Standard InCHIKey:	QNVNXPBFKQJAIB-SZXRKYFWSA-N
Standard InCHI:	InChI=1S/C26H30N2O9/c1-2-12-15(9-18-20-14(7-8-27-18)13-5-3-4-6-17(13)28-20)16(24(33)34)11-35-25(12)37-26-23(32)22(31)21(30)19(10-29)36-26/h2-6,11-12,15,19,21-23,25-26,28-32H,1,7-10H2,(H,33,34)/t12?,15?,19-,21-,22+,23-,25+,26+/m1/s1
SMILES:	OC[C@H]1O[C@@H](O[C@@H]2OC=C(C(C2C=C)CC2=NCCc3c2[nH]c2c3cccc2)C(=O)O)[C@@H]([C@H]([C@@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL528769
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	=	52300.0	nM	PMID[545692]

☑ 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 NPC476115 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	249
0.1-0.2	1127
0.2-0.3	3944
0.3-0.4	13635
0.4-0.5	17357
0.5-0.6	4150
0.6-0.7	1873
0.7-0.8	331
0.8-0.85	14
0.85-0.9	11
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9728	High Similarity	NPC474905
0.9223	High Similarity	NPC476114
0.9031	High Similarity	NPC82070
0.8806	High Similarity	NPC475271
0.8794	High Similarity	NPC52254
0.8744	High Similarity	NPC174788
0.8434	Intermediate Similarity	NPC477548
0.8302	Intermediate Similarity	NPC57453
0.8049	Intermediate Similarity	NPC313640
0.803	Intermediate Similarity	NPC128265
0.803	Intermediate Similarity	NPC199851
0.803	Intermediate Similarity	NPC294909
0.803	Intermediate Similarity	NPC254240
0.803	Intermediate Similarity	NPC312870
0.798	Intermediate Similarity	NPC50997
0.798	Intermediate Similarity	NPC160127
0.7857	Intermediate Similarity	NPC473800
0.7833	Intermediate Similarity	NPC18661
0.7799	Intermediate Similarity	NPC249428
0.7704	Intermediate Similarity	NPC102338
0.7704	Intermediate Similarity	NPC111602
0.7704	Intermediate Similarity	NPC175474
0.7704	Intermediate Similarity	NPC63199
0.7704	Intermediate Similarity	NPC196251
0.7704	Intermediate Similarity	NPC46413
0.7665	Intermediate Similarity	NPC472112
0.7629	Intermediate Similarity	NPC322043
0.7629	Intermediate Similarity	NPC327373
0.7629	Intermediate Similarity	NPC325093
0.76	Intermediate Similarity	NPC220151
0.76	Intermediate Similarity	NPC19692
0.7593	Intermediate Similarity	NPC472762
0.7588	Intermediate Similarity	NPC472113
0.7586	Intermediate Similarity	NPC49196
0.7586	Intermediate Similarity	NPC79129
0.7586	Intermediate Similarity	NPC313985
0.7586	Intermediate Similarity	NPC195461
0.7586	Intermediate Similarity	NPC249150
0.7586	Intermediate Similarity	NPC81654
0.7577	Intermediate Similarity	NPC71037
0.7576	Intermediate Similarity	NPC469470
0.7576	Intermediate Similarity	NPC469501
0.7574	Intermediate Similarity	NPC50503
0.7571	Intermediate Similarity	NPC234078
0.7571	Intermediate Similarity	NPC229348
0.7571	Intermediate Similarity	NPC221100
0.7565	Intermediate Similarity	NPC270009
0.7551	Intermediate Similarity	NPC318020
0.7538	Intermediate Similarity	NPC472108
0.7538	Intermediate Similarity	NPC139291
0.7525	Intermediate Similarity	NPC182814
0.7512	Intermediate Similarity	NPC20593
0.7512	Intermediate Similarity	NPC476874
0.7488	Intermediate Similarity	NPC52557
0.7475	Intermediate Similarity	NPC328798
0.7475	Intermediate Similarity	NPC325775
0.7451	Intermediate Similarity	NPC241024
0.745	Intermediate Similarity	NPC472097
0.745	Intermediate Similarity	NPC127647
0.7449	Intermediate Similarity	NPC472444
0.7448	Intermediate Similarity	NPC34508
0.7441	Intermediate Similarity	NPC244856
0.7431	Intermediate Similarity	NPC79107
0.7431	Intermediate Similarity	NPC475424
0.7424	Intermediate Similarity	NPC315555
0.7424	Intermediate Similarity	NPC235684
0.7413	Intermediate Similarity	NPC55493
0.74	Intermediate Similarity	NPC314333
0.7396	Intermediate Similarity	NPC6982
0.7389	Intermediate Similarity	NPC472293
0.7385	Intermediate Similarity	NPC472443
0.7385	Intermediate Similarity	NPC21638
0.7371	Intermediate Similarity	NPC471284
0.7368	Intermediate Similarity	NPC46225
0.7366	Intermediate Similarity	NPC470507
0.7366	Intermediate Similarity	NPC472297
0.7366	Intermediate Similarity	NPC471458
0.7366	Intermediate Similarity	NPC192674
0.7366	Intermediate Similarity	NPC472296
0.7363	Intermediate Similarity	NPC129909
0.736	Intermediate Similarity	NPC469358
0.7358	Intermediate Similarity	NPC235900
0.7349	Intermediate Similarity	NPC281049
0.7346	Intermediate Similarity	NPC234999
0.734	Intermediate Similarity	NPC181502
0.734	Intermediate Similarity	NPC85066
0.7333	Intermediate Similarity	NPC127677
0.733	Intermediate Similarity	NPC214428
0.7327	Intermediate Similarity	NPC472292
0.7324	Intermediate Similarity	NPC236424
0.7324	Intermediate Similarity	NPC306644
0.7313	Intermediate Similarity	NPC206967
0.7306	Intermediate Similarity	NPC470498
0.7304	Intermediate Similarity	NPC245916
0.7304	Intermediate Similarity	NPC231342
0.7302	Intermediate Similarity	NPC312645
0.73	Intermediate Similarity	NPC119700
0.7299	Intermediate Similarity	NPC469743
0.7296	Intermediate Similarity	NPC213468
0.729	Intermediate Similarity	NPC274842
0.7286	Intermediate Similarity	NPC244741
0.7285	Intermediate Similarity	NPC33949
0.7282	Intermediate Similarity	NPC32200
0.7277	Intermediate Similarity	NPC475778
0.7277	Intermediate Similarity	NPC111732
0.7277	Intermediate Similarity	NPC151976
0.7273	Intermediate Similarity	NPC472110
0.7273	Intermediate Similarity	NPC472109
0.7265	Intermediate Similarity	NPC89987
0.7264	Intermediate Similarity	NPC61435
0.7256	Intermediate Similarity	NPC288349
0.7255	Intermediate Similarity	NPC276517
0.7248	Intermediate Similarity	NPC2395
0.7245	Intermediate Similarity	NPC15573
0.7245	Intermediate Similarity	NPC183662
0.7245	Intermediate Similarity	NPC217372
0.7243	Intermediate Similarity	NPC472291
0.7238	Intermediate Similarity	NPC277350
0.7238	Intermediate Similarity	NPC238457
0.7236	Intermediate Similarity	NPC258480
0.7236	Intermediate Similarity	NPC470003
0.7233	Intermediate Similarity	NPC102008
0.7231	Intermediate Similarity	NPC472586
0.7228	Intermediate Similarity	NPC329858
0.7225	Intermediate Similarity	NPC98715
0.7225	Intermediate Similarity	NPC311276
0.7222	Intermediate Similarity	NPC96131
0.7222	Intermediate Similarity	NPC192270
0.7217	Intermediate Similarity	NPC284102
0.7214	Intermediate Similarity	NPC472323
0.7212	Intermediate Similarity	NPC471944
0.7212	Intermediate Similarity	NPC300183
0.7211	Intermediate Similarity	NPC473320
0.7208	Intermediate Similarity	NPC219336
0.7206	Intermediate Similarity	NPC269886
0.7206	Intermediate Similarity	NPC247735
0.7206	Intermediate Similarity	NPC472295
0.7206	Intermediate Similarity	NPC81802
0.7206	Intermediate Similarity	NPC472210
0.7204	Intermediate Similarity	NPC225821
0.7202	Intermediate Similarity	NPC317430
0.7202	Intermediate Similarity	NPC78020
0.7198	Intermediate Similarity	NPC476516
0.7196	Intermediate Similarity	NPC207020
0.7188	Intermediate Similarity	NPC475720
0.7188	Intermediate Similarity	NPC474192
0.7178	Intermediate Similarity	NPC34271
0.7177	Intermediate Similarity	NPC123019
0.7176	Intermediate Similarity	NPC74969
0.7176	Intermediate Similarity	NPC204491
0.7172	Intermediate Similarity	NPC469896
0.717	Intermediate Similarity	NPC258062
0.7164	Intermediate Similarity	NPC66210
0.7163	Intermediate Similarity	NPC89508
0.7162	Intermediate Similarity	NPC57690
0.7157	Intermediate Similarity	NPC326575
0.7157	Intermediate Similarity	NPC293472
0.7156	Intermediate Similarity	NPC473105
0.7151	Intermediate Similarity	NPC37548
0.715	Intermediate Similarity	NPC250129
0.715	Intermediate Similarity	NPC149708
0.715	Intermediate Similarity	NPC306376
0.715	Intermediate Similarity	NPC165201
0.7149	Intermediate Similarity	NPC141428
0.7149	Intermediate Similarity	NPC472435
0.7149	Intermediate Similarity	NPC235885
0.7143	Intermediate Similarity	NPC149155
0.7143	Intermediate Similarity	NPC141353
0.7143	Intermediate Similarity	NPC189812
0.7143	Intermediate Similarity	NPC285469
0.7143	Intermediate Similarity	NPC203468
0.7143	Intermediate Similarity	NPC165599
0.7143	Intermediate Similarity	NPC329688
0.7143	Intermediate Similarity	NPC110500
0.7135	Intermediate Similarity	NPC40779
0.713	Intermediate Similarity	NPC97388
0.7123	Intermediate Similarity	NPC88008
0.7121	Intermediate Similarity	NPC283219
0.7116	Intermediate Similarity	NPC87856
0.7114	Intermediate Similarity	NPC280290
0.7113	Intermediate Similarity	NPC154293
0.7107	Intermediate Similarity	NPC267885
0.7107	Intermediate Similarity	NPC24594
0.7107	Intermediate Similarity	NPC472122
0.7105	Intermediate Similarity	NPC469762
0.7103	Intermediate Similarity	NPC475165
0.7098	Intermediate Similarity	NPC473806
0.7098	Intermediate Similarity	NPC471634
0.7097	Intermediate Similarity	NPC152768
0.7097	Intermediate Similarity	NPC148183
0.7095	Intermediate Similarity	NPC474116
0.7095	Intermediate Similarity	NPC162730
0.7095	Intermediate Similarity	NPC193761
0.7092	Intermediate Similarity	NPC472123
0.7085	Intermediate Similarity	NPC15840
0.7083	Intermediate Similarity	NPC267965
0.7083	Intermediate Similarity	NPC473547
0.7079	Intermediate Similarity	NPC311858
0.7071	Intermediate Similarity	NPC14325
0.7071	Intermediate Similarity	NPC28848

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 NPC476115 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	170
0.1-0.2	442
0.2-0.3	630
0.3-0.4	1579
0.4-0.5	3225
0.5-0.6	2456
0.6-0.7	593
0.7-0.8	53
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
0.803	Intermediate Similarity	NPD4500	Approved
0.803	Intermediate Similarity	NPD4501	Approved
0.7586	Intermediate Similarity	NPD4600	Approved
0.7586	Intermediate Similarity	NPD4601	Approved
0.7537	Intermediate Similarity	NPD6248	Phase 2
0.7537	Intermediate Similarity	NPD6249	Phase 2
0.7465	Intermediate Similarity	NPD8325	Phase 3
0.7465	Intermediate Similarity	NPD8326	Phase 3
0.7465	Intermediate Similarity	NPD8327	Clinical (unspecified phase)
0.7455	Intermediate Similarity	NPD8372	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD43	Approved
0.7448	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7448	Intermediate Similarity	NPD6182	Approved
0.7438	Intermediate Similarity	NPD5003	Discontinued
0.7436	Intermediate Similarity	NPD5899	Approved
0.7436	Intermediate Similarity	NPD5898	Approved
0.7436	Intermediate Similarity	NPD5897	Approved
0.74	Intermediate Similarity	NPD4499	Approved
0.7366	Intermediate Similarity	NPD3800	Clinical (unspecified phase)
0.7363	Intermediate Similarity	NPD3785	Clinical (unspecified phase)
0.736	Intermediate Similarity	NPD2094	Phase 2
0.736	Intermediate Similarity	NPD2092	Phase 2
0.736	Intermediate Similarity	NPD2095	Phase 2
0.7323	Intermediate Similarity	NPD2096	Phase 2
0.7323	Intermediate Similarity	NPD2091	Phase 2
0.7308	Intermediate Similarity	NPD5487	Phase 1
0.7299	Intermediate Similarity	NPD4506	Discontinued
0.7277	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.7268	Intermediate Similarity	NPD6206	Phase 1
0.7264	Intermediate Similarity	NPD4900	Clinical (unspecified phase)
0.7264	Intermediate Similarity	NPD4334	Discontinued
0.7251	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7957	Phase 1
0.7238	Intermediate Similarity	NPD4901	Clinical (unspecified phase)
0.7238	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7778	Approved
0.7233	Intermediate Similarity	NPD7777	Approved
0.7233	Intermediate Similarity	NPD6261	Phase 3
0.7233	Intermediate Similarity	NPD53	Approved
0.7216	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7202	Intermediate Similarity	NPD2844	Phase 3
0.7196	Intermediate Similarity	NPD6657	Clinical (unspecified phase)
0.719	Intermediate Similarity	NPD5901	Discontinued
0.7163	Intermediate Similarity	NPD3795	Approved
0.7163	Intermediate Similarity	NPD3794	Approved
0.7143	Intermediate Similarity	NPD482	Approved
0.7143	Intermediate Similarity	NPD2565	Phase 2
0.7143	Intermediate Similarity	NPD2564	Approved
0.7143	Intermediate Similarity	NPD6176	Phase 1
0.713	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD3393	Approved
0.7097	Intermediate Similarity	NPD3394	Approved
0.7097	Intermediate Similarity	NPD3389	Approved
0.7095	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.7089	Intermediate Similarity	NPD2510	Approved
0.7089	Intermediate Similarity	NPD2509	Approved
0.7081	Intermediate Similarity	NPD6479	Discontinued
0.7079	Intermediate Similarity	NPD5444	Phase 1
0.7073	Intermediate Similarity	NPD4315	Phase 2
0.7062	Intermediate Similarity	NPD8072	Approved
0.7062	Intermediate Similarity	NPD2121	Clinical (unspecified phase)
0.7051	Intermediate Similarity	NPD4897	Phase 2
0.7032	Intermediate Similarity	NPD7878	Phase 2
0.7015	Intermediate Similarity	NPD5596	Phase 2
0.701	Intermediate Similarity	NPD7233	Approved
0.701	Intermediate Similarity	NPD7234	Approved
0.7009	Intermediate Similarity	NPD8423	Phase 2
0.7009	Intermediate Similarity	NPD8399	Phase 1
0.7005	Intermediate Similarity	NPD4602	Approved
0.7	Intermediate Similarity	NPD6770	Approved
0.6977	Remote Similarity	NPD6529	Discontinued
0.6967	Remote Similarity	NPD7727	Phase 2
0.6947	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6934	Remote Similarity	NPD8073	Approved
0.6916	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6916	Remote Similarity	NPD6732	Clinical (unspecified phase)
0.6915	Remote Similarity	NPD5473	Discontinued
0.6912	Remote Similarity	NPD7470	Discontinued
0.6901	Remote Similarity	NPD3777	Phase 3
0.69	Remote Similarity	NPD6642	Approved
0.69	Remote Similarity	NPD6641	Approved
0.6898	Remote Similarity	NPD5835	Phase 3
0.6898	Remote Similarity	NPD5834	Phase 3
0.6892	Remote Similarity	NPD3280	Approved
0.6888	Remote Similarity	NPD7708	Approved
0.6884	Remote Similarity	NPD5065	Approved
0.6878	Remote Similarity	NPD5632	Approved
0.6878	Remote Similarity	NPD4948	Discontinued
0.6866	Remote Similarity	NPD4076	Approved
0.6866	Remote Similarity	NPD4079	Approved
0.6861	Remote Similarity	NPD5506	Approved
0.6861	Remote Similarity	NPD5507	Approved
0.6846	Remote Similarity	NPD7955	Approved
0.6846	Remote Similarity	NPD7956	Approved
0.6842	Remote Similarity	NPD4463	Approved
0.6842	Remote Similarity	NPD4462	Approved
0.684	Remote Similarity	NPD484	Approved
0.6839	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6834	Remote Similarity	NPD750	Phase 2
0.6822	Remote Similarity	NPD2920	Discontinued
0.6818	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6816	Remote Similarity	NPD3506	Approved
0.6816	Remote Similarity	NPD3505	Approved
0.6816	Remote Similarity	NPD2144	Approved
0.6814	Remote Similarity	NPD6178	Phase 3
0.681	Remote Similarity	NPD5512	Phase 3
0.6804	Remote Similarity	NPD7594	Clinical (unspecified phase)
0.6802	Remote Similarity	NPD4554	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD8374	Phase 3
0.6798	Remote Similarity	NPD3038	Discontinued
0.6792	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.6791	Remote Similarity	NPD8114	Approved
0.6791	Remote Similarity	NPD8115	Approved
0.6789	Remote Similarity	NPD7998	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8037	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD8036	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8468	Phase 2
0.678	Remote Similarity	NPD5075	Discontinued
0.6776	Remote Similarity	NPD7803	Approved
0.6766	Remote Similarity	NPD2381	Approved
0.6766	Remote Similarity	NPD5104	Approved
0.6766	Remote Similarity	NPD2382	Approved
0.6766	Remote Similarity	NPD2380	Approved
0.6763	Remote Similarity	NPD1534	Approved
0.6759	Remote Similarity	NPD3003	Approved
0.6758	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6758	Remote Similarity	NPD5416	Discontinued
0.6753	Remote Similarity	NPD8329	Phase 3
0.6751	Remote Similarity	NPD2915	Discontinued
0.6739	Remote Similarity	NPD4885	Approved
0.6738	Remote Similarity	NPD1592	Phase 3
0.6736	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6734	Remote Similarity	NPD1325	Approved
0.6734	Remote Similarity	NPD1326	Approved
0.6729	Remote Similarity	NPD7817	Phase 1
0.6713	Remote Similarity	NPD56	Approved
0.6713	Remote Similarity	NPD8283	Approved
0.6713	Remote Similarity	NPD8282	Approved
0.6712	Remote Similarity	NPD5072	Discontinued
0.6712	Remote Similarity	NPD7809	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD5088	Discontinued
0.67	Remote Similarity	NPD5398	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5069	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD5501	Discontinued
0.6683	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD7944	Discontinued
0.6682	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6682	Remote Similarity	NPD5427	Suspended
0.6681	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5417	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5744	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD7797	Approved
0.6667	Remote Similarity	NPD5902	Approved
0.6667	Remote Similarity	NPD7796	Approved
0.6667	Remote Similarity	NPD7946	Pre-registration
0.6667	Remote Similarity	NPD5903	Approved
0.6652	Remote Similarity	NPD7395	Discontinued
0.6652	Remote Similarity	NPD7548	Discontinued
0.6651	Remote Similarity	NPD6550	Discontinued
0.6651	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.665	Remote Similarity	NPD3436	Approved
0.6649	Remote Similarity	NPD5020	Approved
0.6638	Remote Similarity	NPD4086	Phase 1
0.6638	Remote Similarity	NPD7558	Phase 2
0.6637	Remote Similarity	NPD7218	Clinical (unspecified phase)
0.6636	Remote Similarity	NPD8098	Approved
0.6636	Remote Similarity	NPD5426	Phase 3
0.6636	Remote Similarity	NPD1768	Approved
0.6635	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.6635	Remote Similarity	NPD6141	Clinical (unspecified phase)
0.6634	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6632	Remote Similarity	NPD6158	Phase 2
0.6621	Remote Similarity	NPD2916	Discontinued
0.6619	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6616	Remote Similarity	NPD5138	Approved
0.6616	Remote Similarity	NPD5140	Approved
0.6612	Remote Similarity	NPD8370	Discontinued
0.6609	Remote Similarity	NPD7781	Approved
0.6609	Remote Similarity	NPD7780	Approved
0.6606	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5067	Phase 2
0.6606	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6606	Remote Similarity	NPD5066	Phase 2
0.6606	Remote Similarity	NPD5475	Discontinued
0.6604	Remote Similarity	NPD4427	Phase 2
0.6593	Remote Similarity	NPD6242	Discontinued
0.6592	Remote Similarity	NPD7707	Approved
0.6592	Remote Similarity	NPD4667	Clinical (unspecified phase)
0.6591	Remote Similarity	NPD4520	Approved
0.6587	Remote Similarity	NPD4426	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6452	Discontinued
0.6585	Remote Similarity	NPD8464	Clinical (unspecified phase)
0.6585	Remote Similarity	NPD6595	Phase 3
0.6582	Remote Similarity	NPD6517	Phase 3
0.6579	Remote Similarity	NPD7716	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