Structure

Physi-Chem Properties

Molecular Weight:  428.4
Volume:  493.444
LogP:  7.608
LogD:  5.659
LogS:  -6.545
# Rotatable Bonds:  1
TPSA:  20.23
# H-Bond Aceptor:  1
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.445
Synthetic Accessibility Score:  4.598
Fsp3:  1.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Rejected
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:  -4.822
MDCK Permeability:  7.955817636684515e-06
Pgp-inhibitor:  0.394
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.019
20% Bioavailability (F20%):  0.968
30% Bioavailability (F30%):  0.962

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.058
Plasma Protein Binding (PPB):  94.17312622070312%
Volume Distribution (VD):  1.488
Pgp-substrate:  1.771101951599121%

ADMET: Metabolism

CYP1A2-inhibitor:  0.041
CYP1A2-substrate:  0.267
CYP2C19-inhibitor:  0.064
CYP2C19-substrate:  0.964
CYP2C9-inhibitor:  0.108
CYP2C9-substrate:  0.23
CYP2D6-inhibitor:  0.113
CYP2D6-substrate:  0.447
CYP3A4-inhibitor:  0.316
CYP3A4-substrate:  0.411

ADMET: Excretion

Clearance (CL):  5.016
Half-life (T1/2):  0.023

ADMET: Toxicity

hERG Blockers:  0.822
Human Hepatotoxicity (H-HT):  0.148
Drug-inuced Liver Injury (DILI):  0.058
AMES Toxicity:  0.003
Rat Oral Acute Toxicity:  0.15
Maximum Recommended Daily Dose:  0.06
Skin Sensitization:  0.946
Carcinogencity:  0.083
Eye Corrosion:  0.991
Eye Irritation:  0.583
Respiratory Toxicity:  0.885

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

  Natural Product: NPC162685

Natural Product ID:  NPC162685
Common Name*:   2-[(3S,3As,5Ar,5Br,7As,11As,11Br,13Ar,13Bs)-5A,5B,8,8,11A,13B-Hexamethyl-1,2,3,3A,4,5,6,7,7A,9,10,11,11B,12,13,13A-Hexadecahydrocyclopenta[A]Chrysen-3-Yl]Propan-2-Ol
IUPAC Name:   2-[(3S,3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]propan-2-ol
Synonyms:  
Standard InCHIKey:  PNJBOAVCVAVRGR-UDCAXGDQSA-N
Standard InCHI:  InChI=1S/C30H52O/c1-25(2)15-9-16-28(6)22(25)14-19-30(8)24(28)11-10-23-27(5)17-12-20(26(3,4)31)21(27)13-18-29(23,30)7/h20-24,31H,9-19H2,1-8H3/t20-,21-,22-,23+,24+,27-,28-,29+,30+/m0/s1
SMILES:  C[C@]12CC[C@@H]([C@@H]1CC[C@@]1([C@@H]2CC[C@H]2[C@@]1(C)CC[C@@H]1[C@]2(C)CCCC1(C)C)C)C(O)(C)C
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2448591
PubChem CID:   164874
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0001823] Hopanoids

*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
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. PMID[18619266]
NPO19548 Lepisorus contortus Species Polypodiaceae Eukaryota whole plant Gongshan County, Yunnan, China n.a. PMID[21261296]
NPO19548 Lepisorus contortus Species Polypodiaceae Eukaryota n.a. whole plant n.a. PMID[21261296]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. PMID[21377852]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26552 Plagiochasma intermedium Species Aytoniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1960 Lygodium japonicum Species Lygodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO26552 Plagiochasma intermedium Species Aytoniaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO24093 Drynaria fortunei Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19548 Lepisorus contortus Species Polypodiaceae 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
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT367 Cell Line MDA-N Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT391 Cell Line HCC 2998 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 100000.0 nM PMID[566431]

☑ 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 NPC162685 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
0.871 High Similarity NPC48079
0.8621 High Similarity NPC476735
0.8571 High Similarity NPC473225
0.8571 High Similarity NPC472741
0.8548 High Similarity NPC142712
0.85 High Similarity NPC218585
0.85 High Similarity NPC148174
0.85 High Similarity NPC71460
0.8475 Intermediate Similarity NPC95958
0.8438 Intermediate Similarity NPC254037
0.8438 Intermediate Similarity NPC129829
0.8387 Intermediate Similarity NPC475943
0.8387 Intermediate Similarity NPC243469
0.8387 Intermediate Similarity NPC190827
0.8361 Intermediate Similarity NPC114891
0.8308 Intermediate Similarity NPC231945
0.8308 Intermediate Similarity NPC192192
0.8276 Intermediate Similarity NPC3025
0.8226 Intermediate Similarity NPC69149
0.8182 Intermediate Similarity NPC127094
0.8154 Intermediate Similarity NPC99264
0.8125 Intermediate Similarity NPC63190
0.8095 Intermediate Similarity NPC473276
0.8095 Intermediate Similarity NPC474380
0.8095 Intermediate Similarity NPC41577
0.803 Intermediate Similarity NPC108131
0.803 Intermediate Similarity NPC282454
0.7941 Intermediate Similarity NPC477508
0.7937 Intermediate Similarity NPC167995
0.7937 Intermediate Similarity NPC281540
0.7937 Intermediate Similarity NPC118937
0.7937 Intermediate Similarity NPC159654
0.7931 Intermediate Similarity NPC202146
0.7931 Intermediate Similarity NPC32222
0.791 Intermediate Similarity NPC473279
0.791 Intermediate Similarity NPC109457
0.791 Intermediate Similarity NPC157422
0.791 Intermediate Similarity NPC100586
0.7879 Intermediate Similarity NPC299948
0.7879 Intermediate Similarity NPC66407
0.7879 Intermediate Similarity NPC470830
0.7879 Intermediate Similarity NPC241085
0.7879 Intermediate Similarity NPC107919
0.7846 Intermediate Similarity NPC473230
0.7846 Intermediate Similarity NPC475884
0.7812 Intermediate Similarity NPC472946
0.7812 Intermediate Similarity NPC260116
0.7812 Intermediate Similarity NPC80463
0.7778 Intermediate Similarity NPC292419
0.7778 Intermediate Similarity NPC290791
0.7692 Intermediate Similarity NPC44122
0.7692 Intermediate Similarity NPC42060
0.7681 Intermediate Similarity NPC192638
0.7681 Intermediate Similarity NPC62657
0.7681 Intermediate Similarity NPC25511
0.7679 Intermediate Similarity NPC316035
0.7647 Intermediate Similarity NPC470071
0.7647 Intermediate Similarity NPC252182
0.7647 Intermediate Similarity NPC195530
0.7647 Intermediate Similarity NPC187471
0.7647 Intermediate Similarity NPC1340
0.7636 Intermediate Similarity NPC14552
0.7612 Intermediate Similarity NPC477820
0.7612 Intermediate Similarity NPC196197
0.7606 Intermediate Similarity NPC23884
0.7571 Intermediate Similarity NPC195155
0.7571 Intermediate Similarity NPC231256
0.7571 Intermediate Similarity NPC104387
0.7571 Intermediate Similarity NPC174964
0.7571 Intermediate Similarity NPC97534
0.7571 Intermediate Similarity NPC212879
0.7571 Intermediate Similarity NPC240235
0.7571 Intermediate Similarity NPC178383
0.7541 Intermediate Similarity NPC135438
0.7538 Intermediate Similarity NPC476737
0.7538 Intermediate Similarity NPC27243
0.7536 Intermediate Similarity NPC473238
0.7536 Intermediate Similarity NPC472341
0.7536 Intermediate Similarity NPC153719
0.75 Intermediate Similarity NPC232925
0.75 Intermediate Similarity NPC251201
0.75 Intermediate Similarity NPC42853
0.75 Intermediate Similarity NPC63588
0.75 Intermediate Similarity NPC475728
0.7465 Intermediate Similarity NPC278091
0.7465 Intermediate Similarity NPC475742
0.7465 Intermediate Similarity NPC5767
0.7465 Intermediate Similarity NPC86305
0.7465 Intermediate Similarity NPC93662
0.7465 Intermediate Similarity NPC78067
0.7465 Intermediate Similarity NPC14112
0.7463 Intermediate Similarity NPC475893
0.7458 Intermediate Similarity NPC102336
0.7458 Intermediate Similarity NPC36002
0.7429 Intermediate Similarity NPC304499
0.7429 Intermediate Similarity NPC192501
0.7429 Intermediate Similarity NPC472854
0.7429 Intermediate Similarity NPC10476
0.7429 Intermediate Similarity NPC228994
0.7424 Intermediate Similarity NPC477931
0.7424 Intermediate Similarity NPC268736
0.7397 Intermediate Similarity NPC49599
0.7397 Intermediate Similarity NPC220379
0.7397 Intermediate Similarity NPC49627
0.7391 Intermediate Similarity NPC151018
0.7391 Intermediate Similarity NPC320549
0.7391 Intermediate Similarity NPC127283
0.7391 Intermediate Similarity NPC8004
0.7391 Intermediate Similarity NPC157777
0.7391 Intermediate Similarity NPC111234
0.7391 Intermediate Similarity NPC131506
0.7391 Intermediate Similarity NPC156277
0.7391 Intermediate Similarity NPC58057
0.7391 Intermediate Similarity NPC478103
0.7361 Intermediate Similarity NPC212241
0.7361 Intermediate Similarity NPC119355
0.7361 Intermediate Similarity NPC143133
0.7361 Intermediate Similarity NPC221420
0.7361 Intermediate Similarity NPC298168
0.7361 Intermediate Similarity NPC202540
0.7361 Intermediate Similarity NPC248830
0.7353 Intermediate Similarity NPC469941
0.7353 Intermediate Similarity NPC252032
0.7353 Intermediate Similarity NPC319671
0.7353 Intermediate Similarity NPC476734
0.7353 Intermediate Similarity NPC474962
0.7324 Intermediate Similarity NPC3403
0.7324 Intermediate Similarity NPC91387
0.7324 Intermediate Similarity NPC231680
0.7324 Intermediate Similarity NPC27349
0.7324 Intermediate Similarity NPC317242
0.7324 Intermediate Similarity NPC24014
0.7324 Intermediate Similarity NPC243027
0.7324 Intermediate Similarity NPC270306
0.7324 Intermediate Similarity NPC196136
0.7324 Intermediate Similarity NPC158208
0.7313 Intermediate Similarity NPC130459
0.7313 Intermediate Similarity NPC204233
0.7313 Intermediate Similarity NPC478180
0.7313 Intermediate Similarity NPC474221
0.7286 Intermediate Similarity NPC470610
0.7286 Intermediate Similarity NPC310766
0.7286 Intermediate Similarity NPC232112
0.7286 Intermediate Similarity NPC195489
0.7286 Intermediate Similarity NPC253805
0.7273 Intermediate Similarity NPC477603
0.7273 Intermediate Similarity NPC313795
0.726 Intermediate Similarity NPC102708
0.7258 Intermediate Similarity NPC236588
0.7246 Intermediate Similarity NPC477929
0.7246 Intermediate Similarity NPC45296
0.7231 Intermediate Similarity NPC209686
0.7231 Intermediate Similarity NPC249078
0.7231 Intermediate Similarity NPC236099
0.7222 Intermediate Similarity NPC470145
0.7222 Intermediate Similarity NPC91573
0.7222 Intermediate Similarity NPC163597
0.7206 Intermediate Similarity NPC281203
0.7206 Intermediate Similarity NPC31187
0.7206 Intermediate Similarity NPC100917
0.7206 Intermediate Similarity NPC469724
0.7206 Intermediate Similarity NPC469987
0.7206 Intermediate Similarity NPC180777
0.7206 Intermediate Similarity NPC474756
0.7206 Intermediate Similarity NPC2568
0.7206 Intermediate Similarity NPC260319
0.7206 Intermediate Similarity NPC103647
0.72 Intermediate Similarity NPC73515
0.7183 Intermediate Similarity NPC48795
0.7183 Intermediate Similarity NPC5046
0.7183 Intermediate Similarity NPC145552
0.7183 Intermediate Similarity NPC196358
0.7183 Intermediate Similarity NPC478130
0.7183 Intermediate Similarity NPC254509
0.7183 Intermediate Similarity NPC280026
0.7183 Intermediate Similarity NPC476736
0.7183 Intermediate Similarity NPC167702
0.7183 Intermediate Similarity NPC49168
0.7183 Intermediate Similarity NPC254340
0.7162 Intermediate Similarity NPC472742
0.7162 Intermediate Similarity NPC192744
0.7162 Intermediate Similarity NPC116119
0.7162 Intermediate Similarity NPC80297
0.7162 Intermediate Similarity NPC475727
0.7162 Intermediate Similarity NPC201459
0.7143 Intermediate Similarity NPC247195
0.7143 Intermediate Similarity NPC164045
0.7143 Intermediate Similarity NPC473267
0.7143 Intermediate Similarity NPC469940
0.7123 Intermediate Similarity NPC64081
0.7123 Intermediate Similarity NPC68828
0.7123 Intermediate Similarity NPC171658
0.7123 Intermediate Similarity NPC476233
0.7123 Intermediate Similarity NPC474574
0.7123 Intermediate Similarity NPC66105
0.7123 Intermediate Similarity NPC477227
0.7123 Intermediate Similarity NPC11907
0.7123 Intermediate Similarity NPC477919
0.7123 Intermediate Similarity NPC180199
0.7123 Intermediate Similarity NPC105208

  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 NPC162685 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
0.8 Intermediate Similarity NPD5360 Phase 3
0.8 Intermediate Similarity NPD5361 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7761 Intermediate Similarity NPD4787 Phase 1
0.75 Intermediate Similarity NPD4789 Approved
0.7424 Intermediate Similarity NPD4224 Phase 2
0.7391 Intermediate Similarity NPD6081 Approved
0.7391 Intermediate Similarity NPD4758 Discontinued
0.7391 Intermediate Similarity NPD4808 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD4243 Approved
0.7391 Intermediate Similarity NPD4809 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD3171 Clinical (unspecified phase)
0.7246 Intermediate Similarity NPD4245 Approved
0.7246 Intermediate Similarity NPD4244 Approved
0.7183 Intermediate Similarity NPD4785 Approved
0.7183 Intermediate Similarity NPD6113 Clinical (unspecified phase)
0.7183 Intermediate Similarity NPD4784 Approved
0.7101 Intermediate Similarity NPD3698 Phase 2
0.7101 Intermediate Similarity NPD3699 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD3700 Clinical (unspecified phase)
0.7027 Intermediate Similarity NPD5364 Discontinued
0.6986 Remote Similarity NPD6117 Approved
0.6957 Remote Similarity NPD6705 Phase 1
0.6892 Remote Similarity NPD6116 Phase 1
0.6849 Remote Similarity NPD5275 Approved
0.6849 Remote Similarity NPD4190 Phase 3
0.6849 Remote Similarity NPD7339 Approved
0.6849 Remote Similarity NPD6942 Approved
0.6849 Remote Similarity NPD3702 Approved
0.6842 Remote Similarity NPD6928 Phase 2
0.6842 Remote Similarity NPD7525 Registered
0.68 Remote Similarity NPD6697 Approved
0.68 Remote Similarity NPD6114 Approved
0.68 Remote Similarity NPD6115 Approved
0.68 Remote Similarity NPD6118 Approved
0.6625 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6622 Remote Similarity NPD3703 Phase 2
0.6582 Remote Similarity NPD4788 Approved
0.6552 Remote Similarity NPD386 Approved
0.6552 Remote Similarity NPD388 Approved
0.6494 Remote Similarity NPD4195 Approved
0.6486 Remote Similarity NPD6924 Approved
0.6486 Remote Similarity NPD6926 Approved
0.6438 Remote Similarity NPD5777 Approved
0.6364 Remote Similarity NPD3671 Phase 1
0.6316 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6316 Remote Similarity NPD6933 Approved
0.6282 Remote Similarity NPD7645 Phase 2
0.625 Remote Similarity NPD4221 Approved
0.625 Remote Similarity NPD4223 Phase 3
0.622 Remote Similarity NPD5329 Approved
0.6203 Remote Similarity NPD4748 Discontinued
0.6167 Remote Similarity NPD384 Approved
0.6167 Remote Similarity NPD385 Approved
0.6164 Remote Similarity NPD6922 Approved
0.6164 Remote Similarity NPD6923 Approved
0.6163 Remote Similarity NPD8034 Phase 2
0.6163 Remote Similarity NPD8035 Phase 2
0.6154 Remote Similarity NPD3617 Approved
0.6125 Remote Similarity NPD4692 Approved
0.6125 Remote Similarity NPD4139 Approved
0.6098 Remote Similarity NPD4786 Approved
0.6098 Remote Similarity NPD4197 Approved
0.6081 Remote Similarity NPD7144 Approved
0.6081 Remote Similarity NPD7143 Approved
0.6 Remote Similarity NPD7150 Approved
0.6 Remote Similarity NPD7152 Approved
0.6 Remote Similarity NPD6930 Phase 2
0.6 Remote Similarity NPD7151 Approved
0.6 Remote Similarity NPD6931 Approved
0.5952 Remote Similarity NPD4689 Approved
0.5952 Remote Similarity NPD5205 Approved
0.5952 Remote Similarity NPD4690 Approved
0.5952 Remote Similarity NPD4138 Approved
0.5952 Remote Similarity NPD4688 Approved
0.5952 Remote Similarity NPD4693 Phase 3
0.5932 Remote Similarity NPD367 Approved
0.5909 Remote Similarity NPD8171 Discontinued
0.5882 Remote Similarity NPD4751 Clinical (unspecified phase)
0.5875 Remote Similarity NPD6929 Approved
0.5862 Remote Similarity NPD6700 Approved
0.5862 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5854 Remote Similarity NPD3667 Approved
0.5823 Remote Similarity NPD6932 Approved
0.5814 Remote Similarity NPD4723 Approved
0.5814 Remote Similarity NPD4722 Approved
0.5802 Remote Similarity NPD7509 Discontinued
0.5795 Remote Similarity NPD6703 Approved
0.5795 Remote Similarity NPD6702 Approved
0.5783 Remote Similarity NPD6695 Phase 3
0.5765 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5765 Remote Similarity NPD4694 Approved
0.5765 Remote Similarity NPD5280 Approved
0.5765 Remote Similarity NPD5690 Phase 2
0.5747 Remote Similarity NPD4753 Phase 2
0.5747 Remote Similarity NPD5328 Approved
0.5714 Remote Similarity NPD3665 Phase 1
0.5714 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3133 Approved
0.5714 Remote Similarity NPD3666 Approved
0.5679 Remote Similarity NPD6683 Phase 2
0.5647 Remote Similarity NPD6893 Approved
0.5625 Remote Similarity NPD6925 Approved
0.5625 Remote Similarity NPD5776 Phase 2
0.5618 Remote Similarity NPD6079 Approved
0.561 Remote Similarity NPD7514 Phase 3
0.5604 Remote Similarity NPD7991 Discontinued

  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