Structure

Physi-Chem Properties

Molecular Weight:  504.35
Volume:  532.122
LogP:  3.203
LogD:  3.437
LogS:  -3.735
# Rotatable Bonds:  2
TPSA:  118.22
# H-Bond Aceptor:  6
# H-Bond Donor:  5
# Rings:  5
# Heavy Atoms:  6

MedChem Properties

QED Drug-Likeness Score:  0.363
Synthetic Accessibility Score:  5.238
Fsp3:  0.9
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.535
MDCK Permeability:  4.078561323694885e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.007
Human Intestinal Absorption (HIA):  0.58
20% Bioavailability (F20%):  0.038
30% Bioavailability (F30%):  0.038

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.362
Plasma Protein Binding (PPB):  94.74555206298828%
Volume Distribution (VD):  0.532
Pgp-substrate:  4.399779796600342%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.465
CYP2C19-inhibitor:  0.003
CYP2C19-substrate:  0.898
CYP2C9-inhibitor:  0.023
CYP2C9-substrate:  0.163
CYP2D6-inhibitor:  0.001
CYP2D6-substrate:  0.123
CYP3A4-inhibitor:  0.165
CYP3A4-substrate:  0.159

ADMET: Excretion

Clearance (CL):  3.089
Half-life (T1/2):  0.069

ADMET: Toxicity

hERG Blockers:  0.001
Human Hepatotoxicity (H-HT):  0.198
Drug-inuced Liver Injury (DILI):  0.019
AMES Toxicity:  0.028
Rat Oral Acute Toxicity:  0.359
Maximum Recommended Daily Dose:  0.229
Skin Sensitization:  0.007
Carcinogencity:  0.037
Eye Corrosion:  0.003
Eye Irritation:  0.007
Respiratory Toxicity:  0.522

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

  Natural Product: NPC19376

Natural Product ID:  NPC19376
Common Name*:   8,10,11-Trihydroxy-9-(Hydroxymethyl)-1,2,6A,6B,9,12A-Hexamethyl-2,3,4,5,6,6A,7,8,8A,10,11,12,13,14B-Tetradecahydro-1H-Picene-4A-Carboxylic Acid
IUPAC Name:   8,10,11-trihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
Synonyms:  
Standard InCHIKey:  PRAUVHZJPXOEIF-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C30H48O6/c1-16-9-10-30(25(35)36)12-11-28(5)18(22(30)17(16)2)7-8-21-26(3)13-20(33)24(34)27(4,15-31)23(26)19(32)14-29(21,28)6/h7,16-17,19-24,31-34H,8-15H2,1-6H3,(H,35,36)
SMILES:  CC1CCC2(CCC3(C)C(=CCC4C5(C)CC(C(C(C)(CO)C5C(CC34C)O)O)O)C2C1C)C(=O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL1993179
PubChem CID:   258809
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001553] Triterpenoids

*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
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. DOI[10.1007/s11816-015-0350-y]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. aerial part n.a. PMID[17520525]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. PMID[22966846]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[MetaboLights]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO11144 Centella asiatica Species Apiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO11144 Centella asiatica Species Apiaceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 11066.24 nM PMID[505329]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2123.24 nM PMID[505329]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 65765.78 nM PMID[505329]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 20796.97 nM PMID[505329]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 20183.66 nM PMID[505329]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 38994.2 nM PMID[505329]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 47533.52 nM PMID[505329]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 41783.04 nM PMID[505329]
NPT111 Cell Line K562 Homo sapiens GI50 n.a. 41114.97 nM PMID[505329]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 24266.1 nM PMID[505329]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 24099.05 nM PMID[505329]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 58210.32 nM PMID[505329]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 45394.16 nM PMID[505329]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 21627.19 nM PMID[505329]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 21086.28 nM PMID[505329]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 39902.49 nM PMID[505329]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 22698.65 nM PMID[505329]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 22803.42 nM PMID[505329]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 17498.47 nM PMID[505329]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 43251.38 nM PMID[505329]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 90364.95 nM PMID[505329]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 33419.5 nM PMID[505329]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 20511.62 nM PMID[505329]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 31695.67 nM PMID[505329]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 19408.86 nM PMID[505329]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 35892.19 nM PMID[505329]
NPT392 Cell Line SNB-75 Homo sapiens GI50 n.a. 28119.01 nM PMID[505329]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 5649.37 nM PMID[505329]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 28510.18 nM PMID[505329]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 89330.55 nM PMID[505329]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 83560.3 nM PMID[505329]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 41495.4 nM PMID[505329]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 37411.06 nM PMID[505329]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 21330.45 nM PMID[505329]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[505329]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 45603.69 nM PMID[505329]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 74473.2 nM PMID[505329]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 19230.92 nM PMID[505329]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 19408.86 nM PMID[505329]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 3288.52 nM PMID[505329]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 98401.11 nM PMID[505329]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 19010.78 nM PMID[505329]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 88511.56 nM PMID[505329]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 79615.94 nM PMID[505329]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 30760.97 nM PMID[505329]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 31260.79 nM PMID[505329]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 50003.45 nM PMID[505329]

☑ 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 NPC19376 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC305464
1.0 High Similarity NPC25848
1.0 High Similarity NPC307282
0.9775 High Similarity NPC32407
0.9775 High Similarity NPC231063
0.9775 High Similarity NPC145667
0.9775 High Similarity NPC88116
0.9775 High Similarity NPC263548
0.9775 High Similarity NPC20235
0.9775 High Similarity NPC282395
0.9775 High Similarity NPC299996
0.967 High Similarity NPC43686
0.957 High Similarity NPC256247
0.956 High Similarity NPC73004
0.956 High Similarity NPC173744
0.956 High Similarity NPC201657
0.956 High Similarity NPC204961
0.9551 High Similarity NPC71074
0.9551 High Similarity NPC84319
0.9551 High Similarity NPC52021
0.9551 High Similarity NPC235884
0.9551 High Similarity NPC300351
0.9551 High Similarity NPC25299
0.9551 High Similarity NPC472149
0.9551 High Similarity NPC306541
0.9457 High Similarity NPC106112
0.9457 High Similarity NPC261935
0.9457 High Similarity NPC247139
0.9457 High Similarity NPC9613
0.9451 High Similarity NPC32118
0.9451 High Similarity NPC96916
0.9444 High Similarity NPC307335
0.9444 High Similarity NPC136313
0.9444 High Similarity NPC275809
0.9444 High Similarity NPC74855
0.9438 High Similarity NPC49320
0.9438 High Similarity NPC130278
0.9355 High Similarity NPC271614
0.9355 High Similarity NPC111214
0.9355 High Similarity NPC29765
0.9348 High Similarity NPC207922
0.9348 High Similarity NPC476318
0.9348 High Similarity NPC259733
0.9348 High Similarity NPC158371
0.9348 High Similarity NPC476327
0.9341 High Similarity NPC159365
0.9333 High Similarity NPC475708
0.9326 High Similarity NPC127689
0.9326 High Similarity NPC25906
0.9326 High Similarity NPC234346
0.9326 High Similarity NPC64872
0.9326 High Similarity NPC290972
0.9326 High Similarity NPC121798
0.9326 High Similarity NPC263393
0.9326 High Similarity NPC130520
0.9326 High Similarity NPC59263
0.9326 High Similarity NPC61543
0.9326 High Similarity NPC225585
0.9326 High Similarity NPC293048
0.9326 High Similarity NPC270768
0.9255 High Similarity NPC35239
0.9247 High Similarity NPC255589
0.9247 High Similarity NPC259788
0.9239 High Similarity NPC473240
0.9239 High Similarity NPC198245
0.9231 High Similarity NPC133579
0.9231 High Similarity NPC229281
0.9231 High Similarity NPC474806
0.9222 High Similarity NPC120968
0.9222 High Similarity NPC126369
0.9222 High Similarity NPC477872
0.9222 High Similarity NPC7260
0.9222 High Similarity NPC18872
0.9222 High Similarity NPC227467
0.9222 High Similarity NPC273621
0.9222 High Similarity NPC470589
0.9222 High Similarity NPC290614
0.9222 High Similarity NPC111110
0.9222 High Similarity NPC210037
0.9213 High Similarity NPC52169
0.9213 High Similarity NPC182797
0.9175 High Similarity NPC477877
0.914 High Similarity NPC230151
0.914 High Similarity NPC88847
0.913 High Similarity NPC188102
0.913 High Similarity NPC114159
0.913 High Similarity NPC87095
0.913 High Similarity NPC191412
0.913 High Similarity NPC6818
0.9121 High Similarity NPC966
0.9121 High Similarity NPC187722
0.9121 High Similarity NPC324341
0.9121 High Similarity NPC105189
0.9121 High Similarity NPC282616
0.9121 High Similarity NPC288833
0.9121 High Similarity NPC228784
0.9121 High Similarity NPC155120
0.9111 High Similarity NPC274330
0.9111 High Similarity NPC143232
0.9111 High Similarity NPC198664
0.9101 High Similarity NPC102683
0.9101 High Similarity NPC88716
0.9101 High Similarity NPC51700
0.9101 High Similarity NPC130577
0.9101 High Similarity NPC242468
0.9101 High Similarity NPC18064
0.9101 High Similarity NPC171203
0.9101 High Similarity NPC98442
0.9101 High Similarity NPC68160
0.9101 High Similarity NPC293564
0.9101 High Similarity NPC307426
0.9101 High Similarity NPC142415
0.9053 High Similarity NPC476195
0.9043 High Similarity NPC189880
0.9043 High Similarity NPC476878
0.9043 High Similarity NPC203343
0.9043 High Similarity NPC476879
0.9043 High Similarity NPC312075
0.9032 High Similarity NPC474727
0.9022 High Similarity NPC158059
0.9022 High Similarity NPC118490
0.9022 High Similarity NPC86368
0.9022 High Similarity NPC118519
0.9022 High Similarity NPC202728
0.9011 High Similarity NPC86372
0.9011 High Similarity NPC172361
0.9011 High Similarity NPC193750
0.9011 High Similarity NPC291028
0.9 High Similarity NPC473242
0.9 High Similarity NPC290690
0.9 High Similarity NPC246708
0.9 High Similarity NPC40552
0.9 High Similarity NPC474512
0.9 High Similarity NPC181225
0.9 High Similarity NPC470629
0.9 High Similarity NPC17733
0.8989 High Similarity NPC72638
0.8958 High Similarity NPC118964
0.8958 High Similarity NPC54909
0.8958 High Similarity NPC476132
0.8958 High Similarity NPC233012
0.8947 High Similarity NPC260149
0.8947 High Similarity NPC188833
0.8947 High Similarity NPC58942
0.8936 High Similarity NPC132824
0.8936 High Similarity NPC116457
0.8925 High Similarity NPC296164
0.8925 High Similarity NPC222047
0.8925 High Similarity NPC277399
0.8913 High Similarity NPC471588
0.8913 High Similarity NPC158030
0.8913 High Similarity NPC6255
0.8913 High Similarity NPC38754
0.8913 High Similarity NPC233455
0.8913 High Similarity NPC65120
0.8913 High Similarity NPC4036
0.8913 High Similarity NPC474525
0.8913 High Similarity NPC145067
0.8901 High Similarity NPC470588
0.8901 High Similarity NPC95246
0.8901 High Similarity NPC474972
0.8901 High Similarity NPC161751
0.8878 High Similarity NPC475036
0.883 High Similarity NPC148523
0.883 High Similarity NPC139570
0.883 High Similarity NPC83693
0.8817 High Similarity NPC214756
0.8817 High Similarity NPC295643
0.8817 High Similarity NPC272075
0.8817 High Similarity NPC291373
0.8817 High Similarity NPC298554
0.8812 High Similarity NPC108709
0.8812 High Similarity NPC75747
0.8812 High Similarity NPC7870
0.8812 High Similarity NPC199457
0.8812 High Similarity NPC102914
0.8812 High Similarity NPC68419
0.8812 High Similarity NPC110139
0.8804 High Similarity NPC46441
0.8804 High Similarity NPC474728
0.8804 High Similarity NPC120840
0.8804 High Similarity NPC113989
0.8788 High Similarity NPC80566
0.8778 High Similarity NPC237344
0.8778 High Similarity NPC213412
0.875 High Similarity NPC174663
0.875 High Similarity NPC477876
0.875 High Similarity NPC477875
0.875 High Similarity NPC164349
0.8737 High Similarity NPC473158
0.8737 High Similarity NPC98874
0.8737 High Similarity NPC327179
0.8737 High Similarity NPC157113
0.8737 High Similarity NPC62516
0.8725 High Similarity NPC179434
0.8723 High Similarity NPC91010
0.8723 High Similarity NPC209868
0.8723 High Similarity NPC78580
0.8723 High Similarity NPC80365
0.8723 High Similarity NPC23621

  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 NPC19376 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8913 High Similarity NPD7515 Phase 2
0.8526 High Similarity NPD7748 Approved
0.8454 Intermediate Similarity NPD7902 Approved
0.8144 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.8144 Intermediate Similarity NPD7900 Approved
0.8065 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD7645 Phase 2
0.7755 Intermediate Similarity NPD8035 Phase 2
0.7755 Intermediate Similarity NPD8034 Phase 2
0.7719 Intermediate Similarity NPD8328 Phase 3
0.7677 Intermediate Similarity NPD6399 Phase 3
0.7658 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD7638 Approved
0.7604 Intermediate Similarity NPD3618 Phase 1
0.7579 Intermediate Similarity NPD4786 Approved
0.7573 Intermediate Similarity NPD7640 Approved
0.7573 Intermediate Similarity NPD7639 Approved
0.7553 Intermediate Similarity NPD3667 Approved
0.7551 Intermediate Similarity NPD5328 Approved
0.7547 Intermediate Similarity NPD5739 Approved
0.7547 Intermediate Similarity NPD6675 Approved
0.7547 Intermediate Similarity NPD6402 Approved
0.7547 Intermediate Similarity NPD7128 Approved
0.75 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7477 Intermediate Similarity NPD6412 Phase 2
0.7407 Intermediate Similarity NPD6899 Approved
0.7407 Intermediate Similarity NPD7320 Approved
0.7407 Intermediate Similarity NPD6881 Approved
0.74 Intermediate Similarity NPD6079 Approved
0.7387 Intermediate Similarity NPD4632 Approved
0.7379 Intermediate Similarity NPD4755 Approved
0.7374 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD7525 Registered
0.7339 Intermediate Similarity NPD6373 Approved
0.7339 Intermediate Similarity NPD6372 Approved
0.7327 Intermediate Similarity NPD4202 Approved
0.7315 Intermediate Similarity NPD5697 Approved
0.7315 Intermediate Similarity NPD5701 Approved
0.7312 Intermediate Similarity NPD6118 Approved
0.7312 Intermediate Similarity NPD6115 Approved
0.7312 Intermediate Similarity NPD6697 Approved
0.7312 Intermediate Similarity NPD6114 Approved
0.7297 Intermediate Similarity NPD8297 Approved
0.7273 Intermediate Similarity NPD7102 Approved
0.7273 Intermediate Similarity NPD6883 Approved
0.7273 Intermediate Similarity NPD4634 Approved
0.7273 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD7290 Approved
0.7248 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD6686 Approved
0.7238 Intermediate Similarity NPD4696 Approved
0.7238 Intermediate Similarity NPD5285 Approved
0.7238 Intermediate Similarity NPD5286 Approved
0.7238 Intermediate Similarity NPD4700 Approved
0.7232 Intermediate Similarity NPD8133 Approved
0.7228 Intermediate Similarity NPD6411 Approved
0.7216 Intermediate Similarity NPD3665 Phase 1
0.7216 Intermediate Similarity NPD3666 Approved
0.7216 Intermediate Similarity NPD3133 Approved
0.7212 Intermediate Similarity NPD6083 Phase 2
0.7212 Intermediate Similarity NPD6084 Phase 2
0.7207 Intermediate Similarity NPD8130 Phase 1
0.7207 Intermediate Similarity NPD6649 Approved
0.7207 Intermediate Similarity NPD6847 Approved
0.7207 Intermediate Similarity NPD6617 Approved
0.7207 Intermediate Similarity NPD6869 Approved
0.7207 Intermediate Similarity NPD6650 Approved
0.7204 Intermediate Similarity NPD6116 Phase 1
0.7193 Intermediate Similarity NPD7115 Discovery
0.7182 Intermediate Similarity NPD6013 Approved
0.7182 Intermediate Similarity NPD6012 Approved
0.7182 Intermediate Similarity NPD6014 Approved
0.7155 Intermediate Similarity NPD6319 Approved
0.7143 Intermediate Similarity NPD6882 Approved
0.7143 Intermediate Similarity NPD7507 Approved
0.7117 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5222 Approved
0.7115 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7115 Intermediate Similarity NPD5221 Approved
0.7115 Intermediate Similarity NPD4697 Phase 3
0.7103 Intermediate Similarity NPD5226 Approved
0.7103 Intermediate Similarity NPD5211 Phase 2
0.7103 Intermediate Similarity NPD5225 Approved
0.7103 Intermediate Similarity NPD5224 Approved
0.7103 Intermediate Similarity NPD4633 Approved
0.7097 Intermediate Similarity NPD6117 Approved
0.7091 Intermediate Similarity NPD6011 Approved
0.7071 Intermediate Similarity NPD7146 Approved
0.7071 Intermediate Similarity NPD6409 Approved
0.7071 Intermediate Similarity NPD6684 Approved
0.7071 Intermediate Similarity NPD5330 Approved
0.7071 Intermediate Similarity NPD7521 Approved
0.7071 Intermediate Similarity NPD7334 Approved
0.7054 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7048 Intermediate Similarity NPD5173 Approved
0.7043 Intermediate Similarity NPD6009 Approved
0.7041 Intermediate Similarity NPD3668 Phase 3
0.7037 Intermediate Similarity NPD5175 Approved
0.7037 Intermediate Similarity NPD5174 Approved
0.703 Intermediate Similarity NPD6101 Approved
0.703 Intermediate Similarity NPD4753 Phase 2
0.703 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD7736 Approved
0.7009 Intermediate Similarity NPD5223 Approved
0.7 Intermediate Similarity NPD3573 Approved
0.699 Remote Similarity NPD5779 Approved
0.699 Remote Similarity NPD5778 Approved
0.6981 Remote Similarity NPD4225 Approved
0.6972 Remote Similarity NPD5141 Approved
0.6967 Remote Similarity NPD7319 Approved
0.6952 Remote Similarity NPD7614 Phase 1
0.6944 Remote Similarity NPD7632 Discontinued
0.6931 Remote Similarity NPD6672 Approved
0.6931 Remote Similarity NPD6903 Approved
0.6931 Remote Similarity NPD5737 Approved
0.6923 Remote Similarity NPD7516 Approved
0.6917 Remote Similarity NPD7492 Approved
0.6909 Remote Similarity NPD4767 Approved
0.6909 Remote Similarity NPD6008 Approved
0.6909 Remote Similarity NPD4768 Approved
0.6882 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6881 Remote Similarity NPD4754 Approved
0.6864 Remote Similarity NPD6054 Approved
0.6864 Remote Similarity NPD8294 Approved
0.6864 Remote Similarity NPD8377 Approved
0.6864 Remote Similarity NPD6059 Approved
0.686 Remote Similarity NPD6616 Approved
0.6857 Remote Similarity NPD5695 Phase 3
0.6847 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6838 Remote Similarity NPD7328 Approved
0.6838 Remote Similarity NPD7327 Approved
0.6833 Remote Similarity NPD7604 Phase 2
0.6822 Remote Similarity NPD5696 Approved
0.681 Remote Similarity NPD6274 Approved
0.6809 Remote Similarity NPD7339 Approved
0.6809 Remote Similarity NPD6942 Approved
0.6807 Remote Similarity NPD8379 Approved
0.6807 Remote Similarity NPD5983 Phase 2
0.6807 Remote Similarity NPD8296 Approved
0.6807 Remote Similarity NPD8335 Approved
0.6807 Remote Similarity NPD8033 Approved
0.6807 Remote Similarity NPD8380 Approved
0.6807 Remote Similarity NPD8378 Approved
0.6804 Remote Similarity NPD4695 Discontinued
0.6803 Remote Similarity NPD8293 Discontinued
0.6803 Remote Similarity NPD7078 Approved
0.6786 Remote Similarity NPD4730 Approved
0.6786 Remote Similarity NPD4729 Approved
0.6786 Remote Similarity NPD5128 Approved
0.678 Remote Similarity NPD7101 Approved
0.678 Remote Similarity NPD7100 Approved
0.675 Remote Similarity NPD6370 Approved
0.6737 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6733 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6733 Remote Similarity NPD5279 Phase 3
0.6731 Remote Similarity NPD5281 Approved
0.6731 Remote Similarity NPD5284 Approved
0.6721 Remote Similarity NPD6336 Discontinued
0.6698 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6698 Remote Similarity NPD5210 Approved
0.6698 Remote Similarity NPD4629 Approved
0.6695 Remote Similarity NPD6335 Approved
0.6667 Remote Similarity NPD7503 Approved
0.6667 Remote Similarity NPD5250 Approved
0.6667 Remote Similarity NPD5248 Approved
0.6667 Remote Similarity NPD6016 Approved
0.6667 Remote Similarity NPD5247 Approved
0.6667 Remote Similarity NPD6868 Approved
0.6667 Remote Similarity NPD4223 Phase 3
0.6667 Remote Similarity NPD4221 Approved
0.6667 Remote Similarity NPD6908 Approved
0.6667 Remote Similarity NPD5251 Approved
0.6667 Remote Similarity NPD5249 Phase 3
0.6667 Remote Similarity NPD6015 Approved
0.6667 Remote Similarity NPD6909 Approved
0.6636 Remote Similarity NPD7732 Phase 3
0.6635 Remote Similarity NPD6698 Approved
0.6635 Remote Similarity NPD46 Approved
0.6634 Remote Similarity NPD5329 Approved
0.6632 Remote Similarity NPD3703 Phase 2
0.6612 Remote Similarity NPD5988 Approved
0.661 Remote Similarity NPD6317 Approved
0.6609 Remote Similarity NPD5215 Approved
0.6609 Remote Similarity NPD5217 Approved
0.6609 Remote Similarity NPD5216 Approved
0.66 Remote Similarity NPD4788 Approved
0.6571 Remote Similarity NPD7637 Suspended
0.6569 Remote Similarity NPD6098 Approved
0.6557 Remote Similarity NPD6067 Discontinued
0.6555 Remote Similarity NPD6313 Approved
0.6555 Remote Similarity NPD6314 Approved
0.6545 Remote Similarity NPD5344 Discontinued
0.6538 Remote Similarity NPD6904 Approved
0.6538 Remote Similarity NPD6673 Approved
0.6538 Remote Similarity NPD6080 Approved
0.6535 Remote Similarity NPD4197 Approved
0.6529 Remote Similarity NPD8513 Phase 3
0.6529 Remote Similarity NPD6921 Approved
0.6529 Remote Similarity NPD8517 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