Structure

Physi-Chem Properties

Molecular Weight:  442.38
Volume:  499.598
LogP:  5.94
LogD:  5.122
LogS:  -5.222
# Rotatable Bonds:  0
TPSA:  40.46
# H-Bond Aceptor:  2
# H-Bond Donor:  2
# Rings:  5
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.397
Synthetic Accessibility Score:  4.964
Fsp3:  0.933
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:  -4.943
MDCK Permeability:  2.452184162393678e-05
Pgp-inhibitor:  0.768
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.957
30% Bioavailability (F30%):  0.4

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.254
Plasma Protein Binding (PPB):  95.01288604736328%
Volume Distribution (VD):  0.985
Pgp-substrate:  2.7147786617279053%

ADMET: Metabolism

CYP1A2-inhibitor:  0.045
CYP1A2-substrate:  0.228
CYP2C19-inhibitor:  0.057
CYP2C19-substrate:  0.922
CYP2C9-inhibitor:  0.172
CYP2C9-substrate:  0.213
CYP2D6-inhibitor:  0.03
CYP2D6-substrate:  0.697
CYP3A4-inhibitor:  0.427
CYP3A4-substrate:  0.347

ADMET: Excretion

Clearance (CL):  6.347
Half-life (T1/2):  0.116

ADMET: Toxicity

hERG Blockers:  0.159
Human Hepatotoxicity (H-HT):  0.251
Drug-inuced Liver Injury (DILI):  0.017
AMES Toxicity:  0.002
Rat Oral Acute Toxicity:  0.932
Maximum Recommended Daily Dose:  0.967
Skin Sensitization:  0.609
Carcinogencity:  0.029
Eye Corrosion:  0.338
Eye Irritation:  0.058
Respiratory Toxicity:  0.983

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

  Natural Product: NPC211009

Natural Product ID:  NPC211009
Common Name*:   (3S,4Ar,6Ar,6Ar,6Br,8S,8As,12S,12As,14Ar,14Br)-4,4,6A,6B,8A,12,14B-Heptamethyl-11-Methylidene-1,2,3,4A,5,6,6A,7,8,9,10,12,12A,13,14,14A-Hexadecahydropicene-3,8-Diol
IUPAC Name:   (3S,4aR,6aR,6aR,6bR,8S,8aS,12S,12aS,14aR,14bR)-4,4,6a,6b,8a,12,14b-heptamethyl-11-methylidene-1,2,3,4a,5,6,6a,7,8,9,10,12,12a,13,14,14a-hexadecahydropicene-3,8-diol
Synonyms:  
Standard InCHIKey:  IOPDFSGGBHSXSV-ZPWDLUOLSA-N
Standard InCHI:  InChI=1S/C30H50O2/c1-18-11-14-28(6)24(32)17-30(8)20(25(28)19(18)2)9-10-22-27(5)15-13-23(31)26(3,4)21(27)12-16-29(22,30)7/h19-25,31-32H,1,9-17H2,2-8H3/t19-,20-,21+,22-,23+,24+,25+,27+,28-,29-,30-/m1/s1
SMILES:  C=C1CC[C@]2(C)[C@H](C[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@@H](C(C)(C)[C@@H]5CC[C@@]34C)O)[C@@H]2[C@@H]1C)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL2001382
PubChem CID:   397932
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
NPO17782 Inula britannica Species Asteraceae Eukaryota flowers n.a. n.a. PMID[16643020]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[27276091]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9124 Inula japonica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17782 Inula britannica Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9124 Inula japonica Species Asteraceae 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. 8531.0 nM PMID[571491]
NPT368 Cell Line SN12C Homo sapiens GI50 n.a. 2523.48 nM PMID[571491]
NPT370 Cell Line NCI-H23 Homo sapiens GI50 n.a. 2477.42 nM PMID[571491]
NPT369 Cell Line ACHN Homo sapiens GI50 n.a. 2113.49 nM PMID[571491]
NPT371 Cell Line UO-31 Homo sapiens GI50 n.a. 2500.35 nM PMID[571491]
NPT372 Cell Line HOP-92 Homo sapiens GI50 n.a. 1986.09 nM PMID[571491]
NPT116 Cell Line HL-60 Homo sapiens GI50 n.a. 1534.62 nM PMID[571491]
NPT374 Cell Line SF-539 Homo sapiens GI50 n.a. 2454.71 nM PMID[571491]
NPT90 Cell Line DU-145 Homo sapiens GI50 n.a. 4570.88 nM PMID[571491]
NPT375 Cell Line Malme-3M Homo sapiens GI50 n.a. 3250.87 nM PMID[571491]
NPT373 Cell Line SK-MEL-5 Homo sapiens GI50 n.a. 5164.16 nM PMID[571491]
NPT376 Cell Line A498 Homo sapiens GI50 n.a. 2157.74 nM PMID[571491]
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 n.a. 2371.37 nM PMID[571491]
NPT112 Cell Line MOLT-4 Homo sapiens GI50 n.a. 3221.07 nM PMID[571491]
NPT379 Cell Line HOP-62 Homo sapiens GI50 n.a. 2238.72 nM PMID[571491]
NPT378 Cell Line NCI/ADR-RES Homo sapiens GI50 n.a. 3265.88 nM PMID[571491]
NPT380 Cell Line U-251 Homo sapiens GI50 n.a. 1725.84 nM PMID[571491]
NPT381 Cell Line OVCAR-8 Homo sapiens GI50 n.a. 1853.53 nM PMID[571491]
NPT382 Cell Line OVCAR-5 Homo sapiens GI50 n.a. 4246.2 nM PMID[571491]
NPT383 Cell Line SNB-19 Homo sapiens GI50 n.a. 2317.39 nM PMID[571491]
NPT82 Cell Line MDA-MB-231 Homo sapiens GI50 n.a. 1963.36 nM PMID[571491]
NPT385 Cell Line SR Homo sapiens GI50 n.a. 100000.0 nM PMID[571491]
NPT384 Cell Line TK-10 Homo sapiens GI50 n.a. 5623.41 nM PMID[571491]
NPT323 Cell Line SW-620 Homo sapiens GI50 n.a. 4027.17 nM PMID[571491]
NPT455 Cell Line NCI-H522 Homo sapiens GI50 n.a. 1945.36 nM PMID[571491]
NPT386 Cell Line KM12 Homo sapiens GI50 n.a. 3647.54 nM PMID[571491]
NPT387 Cell Line M14 Homo sapiens GI50 n.a. 4655.86 nM PMID[571491]
NPT389 Cell Line RPMI-8226 Homo sapiens GI50 n.a. 100000.0 nM PMID[571491]
NPT388 Cell Line NCI-H322M Homo sapiens GI50 n.a. 2404.36 nM PMID[571491]
NPT456 Cell Line OVCAR-4 Homo sapiens GI50 n.a. 2494.59 nM PMID[571491]
NPT457 Cell Line BT-549 Homo sapiens GI50 n.a. 10023.05 nM PMID[571491]
NPT390 Cell Line LOX IMVI Homo sapiens GI50 n.a. 1986.09 nM PMID[571491]
NPT147 Cell Line SK-MEL-2 Homo sapiens GI50 n.a. 3672.82 nM PMID[571491]
NPT81 Cell Line A549 Homo sapiens GI50 n.a. 2051.16 nM PMID[571491]
NPT148 Cell Line HCT-15 Homo sapiens GI50 n.a. 3243.4 nM PMID[571491]
NPT393 Cell Line HCT-116 Homo sapiens GI50 n.a. 2985.38 nM PMID[571491]
NPT395 Cell Line SF-268 Homo sapiens GI50 n.a. 2280.34 nM PMID[571491]
NPT394 Cell Line EKVX Homo sapiens GI50 n.a. 2999.16 nM PMID[571491]
NPT83 Cell Line MCF7 Homo sapiens GI50 n.a. 2128.14 nM PMID[571491]
NPT306 Cell Line PC-3 Homo sapiens GI50 n.a. 2864.18 nM PMID[571491]
NPT396 Cell Line T47D Homo sapiens GI50 n.a. 2552.7 nM PMID[571491]
NPT146 Cell Line SK-OV-3 Homo sapiens GI50 n.a. 3793.15 nM PMID[571491]
NPT398 Cell Line UACC-62 Homo sapiens GI50 n.a. 7447.32 nM PMID[571491]
NPT397 Cell Line NCI-H460 Homo sapiens GI50 n.a. 2113.49 nM PMID[571491]
NPT308 Cell Line CAKI-1 Homo sapiens GI50 n.a. 2421.03 nM PMID[571491]
NPT400 Cell Line MDA-MB-435 Homo sapiens GI50 n.a. 4216.97 nM PMID[571491]
NPT458 Cell Line IGROV-1 Homo sapiens GI50 n.a. 1999.86 nM PMID[571491]
NPT399 Cell Line SF-295 Homo sapiens GI50 n.a. 3491.4 nM PMID[571491]
NPT402 Cell Line Hs-578T Homo sapiens GI50 n.a. 2691.53 nM PMID[571491]
NPT401 Cell Line 786-0 Homo sapiens GI50 n.a. 2703.96 nM PMID[571491]
NPT403 Cell Line UACC-257 Homo sapiens GI50 n.a. 8072.35 nM PMID[571491]
NPT404 Cell Line CCRF-CEM Homo sapiens GI50 n.a. 5834.45 nM PMID[571491]
NPT405 Cell Line NCI-H226 Homo sapiens GI50 n.a. 5000.35 nM PMID[571491]
NPT139 Cell Line HT-29 Homo sapiens GI50 n.a. 3899.42 nM PMID[571491]
NPT170 Cell Line SK-MEL-28 Homo sapiens GI50 n.a. 4120.98 nM PMID[571491]
NPT407 Cell Line COLO 205 Homo sapiens GI50 n.a. 4226.69 nM PMID[571491]
NPT406 Cell Line RXF 393 Homo sapiens GI50 n.a. 1766.04 nM PMID[571491]

☑ 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 NPC211009 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
0.9851 High Similarity NPC301226
0.971 High Similarity NPC144075
0.9167 High Similarity NPC40394
0.9167 High Similarity NPC34177
0.9167 High Similarity NPC157996
0.9167 High Similarity NPC101475
0.9155 High Similarity NPC178383
0.9155 High Similarity NPC240235
0.9155 High Similarity NPC212879
0.9155 High Similarity NPC104387
0.9155 High Similarity NPC231256
0.9041 High Similarity NPC300499
0.9041 High Similarity NPC253807
0.9041 High Similarity NPC158662
0.9041 High Similarity NPC474989
0.9041 High Similarity NPC196753
0.9041 High Similarity NPC22955
0.9041 High Similarity NPC470396
0.9041 High Similarity NPC230295
0.9041 High Similarity NPC99168
0.9041 High Similarity NPC98386
0.9028 High Similarity NPC122418
0.9028 High Similarity NPC265328
0.9028 High Similarity NPC30590
0.9028 High Similarity NPC78067
0.9028 High Similarity NPC14112
0.9028 High Similarity NPC93662
0.9028 High Similarity NPC120098
0.9028 High Similarity NPC27765
0.9028 High Similarity NPC86305
0.9028 High Similarity NPC290598
0.9028 High Similarity NPC278091
0.9014 High Similarity NPC62657
0.9014 High Similarity NPC25511
0.9014 High Similarity NPC192638
0.8919 High Similarity NPC291379
0.8919 High Similarity NPC53744
0.8904 High Similarity NPC212241
0.8904 High Similarity NPC202540
0.8904 High Similarity NPC119355
0.8904 High Similarity NPC248830
0.8889 High Similarity NPC34700
0.8889 High Similarity NPC138374
0.8857 High Similarity NPC45296
0.88 High Similarity NPC295131
0.8784 High Similarity NPC102708
0.8784 High Similarity NPC42853
0.8767 High Similarity NPC106364
0.875 High Similarity NPC308440
0.875 High Similarity NPC472503
0.875 High Similarity NPC100334
0.8732 High Similarity NPC111234
0.8714 High Similarity NPC210323
0.8684 High Similarity NPC242350
0.8667 High Similarity NPC49627
0.8667 High Similarity NPC116119
0.8667 High Similarity NPC49599
0.8667 High Similarity NPC472742
0.8667 High Similarity NPC80297
0.8667 High Similarity NPC475727
0.8657 High Similarity NPC290791
0.8657 High Similarity NPC292419
0.8649 High Similarity NPC472805
0.8649 High Similarity NPC90979
0.863 High Similarity NPC230704
0.863 High Similarity NPC70982
0.863 High Similarity NPC3403
0.863 High Similarity NPC185536
0.8571 High Similarity NPC304285
0.8571 High Similarity NPC2648
0.8571 High Similarity NPC47763
0.8553 High Similarity NPC475679
0.8533 High Similarity NPC72507
0.8529 High Similarity NPC144650
0.8529 High Similarity NPC101128
0.8514 High Similarity NPC91573
0.8514 High Similarity NPC470766
0.8493 Intermediate Similarity NPC254509
0.8493 Intermediate Similarity NPC49168
0.8493 Intermediate Similarity NPC196358
0.8493 Intermediate Similarity NPC145552
0.8493 Intermediate Similarity NPC5046
0.8472 Intermediate Similarity NPC167706
0.8462 Intermediate Similarity NPC253402
0.8462 Intermediate Similarity NPC159168
0.8442 Intermediate Similarity NPC116202
0.8429 Intermediate Similarity NPC185874
0.8429 Intermediate Similarity NPC269077
0.8429 Intermediate Similarity NPC253303
0.8429 Intermediate Similarity NPC204233
0.8429 Intermediate Similarity NPC139207
0.8406 Intermediate Similarity NPC208198
0.8406 Intermediate Similarity NPC11555
0.8406 Intermediate Similarity NPC60837
0.8406 Intermediate Similarity NPC282619
0.8406 Intermediate Similarity NPC2728
0.8406 Intermediate Similarity NPC172613
0.84 Intermediate Similarity NPC257191
0.84 Intermediate Similarity NPC470758
0.84 Intermediate Similarity NPC470711
0.84 Intermediate Similarity NPC84868
0.84 Intermediate Similarity NPC138502
0.84 Intermediate Similarity NPC307336
0.84 Intermediate Similarity NPC260301
0.84 Intermediate Similarity NPC331618
0.8378 Intermediate Similarity NPC200243
0.8375 Intermediate Similarity NPC187545
0.8356 Intermediate Similarity NPC182717
0.8356 Intermediate Similarity NPC195489
0.8354 Intermediate Similarity NPC238992
0.831 Intermediate Similarity NPC244790
0.831 Intermediate Similarity NPC469987
0.831 Intermediate Similarity NPC475893
0.8289 Intermediate Similarity NPC285761
0.8289 Intermediate Similarity NPC472500
0.8289 Intermediate Similarity NPC472342
0.8289 Intermediate Similarity NPC31828
0.8289 Intermediate Similarity NPC167037
0.8289 Intermediate Similarity NPC472499
0.8289 Intermediate Similarity NPC472501
0.8289 Intermediate Similarity NPC477819
0.8289 Intermediate Similarity NPC138621
0.8289 Intermediate Similarity NPC477817
0.8289 Intermediate Similarity NPC6978
0.8289 Intermediate Similarity NPC301707
0.8289 Intermediate Similarity NPC244385
0.8286 Intermediate Similarity NPC473929
0.8267 Intermediate Similarity NPC38141
0.8267 Intermediate Similarity NPC470749
0.8267 Intermediate Similarity NPC237460
0.8261 Intermediate Similarity NPC68656
0.825 Intermediate Similarity NPC191965
0.825 Intermediate Similarity NPC133954
0.8243 Intermediate Similarity NPC243342
0.8243 Intermediate Similarity NPC91858
0.8243 Intermediate Similarity NPC476736
0.8243 Intermediate Similarity NPC477138
0.8228 Intermediate Similarity NPC475726
0.8228 Intermediate Similarity NPC82538
0.8228 Intermediate Similarity NPC5280
0.8228 Intermediate Similarity NPC246956
0.8228 Intermediate Similarity NPC237795
0.8228 Intermediate Similarity NPC472743
0.8205 Intermediate Similarity NPC328264
0.8194 Intermediate Similarity NPC9942
0.8182 Intermediate Similarity NPC472463
0.8182 Intermediate Similarity NPC80530
0.8182 Intermediate Similarity NPC24504
0.8182 Intermediate Similarity NPC476316
0.8182 Intermediate Similarity NPC273410
0.8158 Intermediate Similarity NPC471798
0.8148 Intermediate Similarity NPC84121
0.8148 Intermediate Similarity NPC137306
0.8148 Intermediate Similarity NPC74363
0.8148 Intermediate Similarity NPC235341
0.8148 Intermediate Similarity NPC475862
0.8148 Intermediate Similarity NPC237344
0.8148 Intermediate Similarity NPC95594
0.8148 Intermediate Similarity NPC213412
0.8148 Intermediate Similarity NPC477579
0.8143 Intermediate Similarity NPC80463
0.8143 Intermediate Similarity NPC260116
0.8143 Intermediate Similarity NPC476737
0.8143 Intermediate Similarity NPC27243
0.8143 Intermediate Similarity NPC258595
0.8133 Intermediate Similarity NPC103822
0.8133 Intermediate Similarity NPC291503
0.8133 Intermediate Similarity NPC477923
0.8133 Intermediate Similarity NPC66566
0.8125 Intermediate Similarity NPC474482
0.8125 Intermediate Similarity NPC264665
0.8125 Intermediate Similarity NPC475745
0.8125 Intermediate Similarity NPC74595
0.8108 Intermediate Similarity NPC471799
0.8108 Intermediate Similarity NPC472506
0.8101 Intermediate Similarity NPC248886
0.8077 Intermediate Similarity NPC13554
0.8077 Intermediate Similarity NPC71535
0.8077 Intermediate Similarity NPC102253
0.8077 Intermediate Similarity NPC78545
0.8077 Intermediate Similarity NPC47149
0.8077 Intermediate Similarity NPC236237
0.8077 Intermediate Similarity NPC322313
0.8056 Intermediate Similarity NPC276616
0.8056 Intermediate Similarity NPC245795
0.8056 Intermediate Similarity NPC94192
0.8052 Intermediate Similarity NPC312328
0.8052 Intermediate Similarity NPC472502
0.8052 Intermediate Similarity NPC475
0.8052 Intermediate Similarity NPC85346
0.8052 Intermediate Similarity NPC65897
0.8052 Intermediate Similarity NPC11908
0.8052 Intermediate Similarity NPC302041
0.8049 Intermediate Similarity NPC171203
0.8049 Intermediate Similarity NPC51700
0.8049 Intermediate Similarity NPC242468
0.8049 Intermediate Similarity NPC142415
0.8049 Intermediate Similarity NPC68160
0.8049 Intermediate Similarity NPC88716
0.8049 Intermediate Similarity NPC98442

  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 NPC211009 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
0.8919 High Similarity NPD7645 Phase 2
0.8077 Intermediate Similarity NPD7525 Registered
0.8025 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7674 Intermediate Similarity NPD7515 Phase 2
0.7662 Intermediate Similarity NPD7339 Approved
0.7662 Intermediate Similarity NPD6942 Approved
0.7564 Intermediate Similarity NPD3701 Clinical (unspecified phase)
0.7303 Intermediate Similarity NPD7748 Approved
0.7273 Intermediate Similarity NPD8034 Phase 2
0.7273 Intermediate Similarity NPD8035 Phase 2
0.7237 Intermediate Similarity NPD4267 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD3618 Phase 1
0.7089 Intermediate Similarity NPD6926 Approved
0.7089 Intermediate Similarity NPD6924 Approved
0.7065 Intermediate Similarity NPD7902 Approved
0.7059 Intermediate Similarity NPD4786 Approved
0.7045 Intermediate Similarity NPD5328 Approved
0.7024 Intermediate Similarity NPD3667 Approved
0.6941 Remote Similarity NPD4788 Approved
0.6923 Remote Similarity NPD4787 Phase 1
0.6914 Remote Similarity NPD6933 Approved
0.6889 Remote Similarity NPD6079 Approved
0.6835 Remote Similarity NPD7152 Approved
0.6835 Remote Similarity NPD4243 Approved
0.6835 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6835 Remote Similarity NPD7150 Approved
0.6835 Remote Similarity NPD7151 Approved
0.6835 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6795 Remote Similarity NPD6923 Approved
0.6795 Remote Similarity NPD6922 Approved
0.6795 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6795 Remote Similarity NPD3699 Clinical (unspecified phase)
0.679 Remote Similarity NPD8264 Approved
0.6786 Remote Similarity NPD7509 Discontinued
0.6786 Remote Similarity NPD4748 Discontinued
0.6739 Remote Similarity NPD7900 Approved
0.6739 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6709 Remote Similarity NPD7144 Approved
0.6709 Remote Similarity NPD7143 Approved
0.6707 Remote Similarity NPD6117 Approved
0.6667 Remote Similarity NPD4785 Approved
0.6667 Remote Similarity NPD3665 Phase 1
0.6667 Remote Similarity NPD4784 Approved
0.6667 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3133 Approved
0.6667 Remote Similarity NPD6929 Approved
0.6667 Remote Similarity NPD3666 Approved
0.6632 Remote Similarity NPD7638 Approved
0.663 Remote Similarity NPD4202 Approved
0.6629 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6627 Remote Similarity NPD6116 Phase 1
0.6588 Remote Similarity NPD6930 Phase 2
0.6588 Remote Similarity NPD6931 Approved
0.6585 Remote Similarity NPD3703 Phase 2
0.6562 Remote Similarity NPD7640 Approved
0.6562 Remote Similarity NPD7639 Approved
0.6548 Remote Similarity NPD6114 Approved
0.6548 Remote Similarity NPD6118 Approved
0.6548 Remote Similarity NPD6115 Approved
0.6548 Remote Similarity NPD6697 Approved
0.65 Remote Similarity NPD4244 Approved
0.65 Remote Similarity NPD4245 Approved
0.6429 Remote Similarity NPD6932 Approved
0.6429 Remote Similarity NPD5776 Phase 2
0.6429 Remote Similarity NPD6925 Approved
0.6421 Remote Similarity NPD5222 Approved
0.6421 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6421 Remote Similarity NPD5221 Approved
0.6421 Remote Similarity NPD4697 Phase 3
0.6418 Remote Similarity NPD385 Approved
0.6418 Remote Similarity NPD384 Approved
0.6395 Remote Similarity NPD6928 Phase 2
0.6386 Remote Similarity NPD5275 Approved
0.6386 Remote Similarity NPD4190 Phase 3
0.6375 Remote Similarity NPD3698 Phase 2
0.6364 Remote Similarity NPD6695 Phase 3
0.6354 Remote Similarity NPD5173 Approved
0.6354 Remote Similarity NPD4755 Approved
0.6353 Remote Similarity NPD7322 Clinical (unspecified phase)
0.6353 Remote Similarity NPD7145 Approved
0.6296 Remote Similarity NPD4789 Approved
0.6292 Remote Similarity NPD3668 Phase 3
0.6292 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6289 Remote Similarity NPD5290 Discontinued
0.6279 Remote Similarity NPD4195 Approved
0.6279 Remote Similarity NPD6683 Phase 2
0.6277 Remote Similarity NPD6399 Phase 3
0.625 Remote Similarity NPD5360 Phase 3
0.625 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6224 Remote Similarity NPD5286 Approved
0.6224 Remote Similarity NPD5285 Approved
0.6224 Remote Similarity NPD4700 Approved
0.6224 Remote Similarity NPD4696 Approved
0.6222 Remote Similarity NPD6893 Approved
0.6207 Remote Similarity NPD7514 Phase 3
0.6207 Remote Similarity NPD7332 Phase 2
0.6196 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6163 Remote Similarity NPD3671 Phase 1
0.6162 Remote Similarity NPD5223 Approved
0.6154 Remote Similarity NPD5279 Phase 3
0.6136 Remote Similarity NPD6898 Phase 1
0.6136 Remote Similarity NPD6902 Approved
0.6129 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6129 Remote Similarity NPD4753 Phase 2
0.6104 Remote Similarity NPD368 Approved
0.61 Remote Similarity NPD5225 Approved
0.61 Remote Similarity NPD7632 Discontinued
0.61 Remote Similarity NPD5224 Approved
0.61 Remote Similarity NPD4633 Approved
0.61 Remote Similarity NPD5226 Approved
0.61 Remote Similarity NPD5211 Phase 2
0.6087 Remote Similarity NPD7524 Approved
0.6087 Remote Similarity NPD7750 Discontinued
0.6078 Remote Similarity NPD5739 Approved
0.6078 Remote Similarity NPD7128 Approved
0.6078 Remote Similarity NPD6675 Approved
0.6078 Remote Similarity NPD6402 Approved
0.6076 Remote Similarity NPD3171 Clinical (unspecified phase)
0.6067 Remote Similarity NPD4223 Phase 3
0.6067 Remote Similarity NPD4221 Approved
0.6044 Remote Similarity NPD5329 Approved
0.604 Remote Similarity NPD4754 Approved
0.604 Remote Similarity NPD5174 Approved
0.604 Remote Similarity NPD5175 Approved
0.6023 Remote Similarity NPD4695 Discontinued
0.5981 Remote Similarity NPD8133 Approved
0.598 Remote Similarity NPD5141 Approved
0.5978 Remote Similarity NPD5330 Approved
0.5978 Remote Similarity NPD7334 Approved
0.5978 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5978 Remote Similarity NPD6684 Approved
0.5978 Remote Similarity NPD7146 Approved
0.5978 Remote Similarity NPD7521 Approved
0.5978 Remote Similarity NPD6409 Approved
0.5977 Remote Similarity NPD3617 Approved
0.5962 Remote Similarity NPD7320 Approved
0.5962 Remote Similarity NPD6899 Approved
0.5962 Remote Similarity NPD6881 Approved
0.596 Remote Similarity NPD4225 Approved
0.5934 Remote Similarity NPD4197 Approved
0.5922 Remote Similarity NPD4768 Approved
0.5922 Remote Similarity NPD4767 Approved
0.5914 Remote Similarity NPD3573 Approved
0.5905 Remote Similarity NPD6372 Approved
0.5905 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5905 Remote Similarity NPD6373 Approved
0.5865 Remote Similarity NPD5701 Approved
0.5865 Remote Similarity NPD5697 Approved
0.5859 Remote Similarity NPD6084 Phase 2
0.5859 Remote Similarity NPD6083 Phase 2
0.5854 Remote Similarity NPD6705 Phase 1
0.5851 Remote Similarity NPD6903 Approved
0.5849 Remote Similarity NPD7102 Approved
0.5849 Remote Similarity NPD7290 Approved
0.5849 Remote Similarity NPD6883 Approved
0.5842 Remote Similarity NPD4159 Approved
0.5833 Remote Similarity NPD7087 Discontinued
0.5833 Remote Similarity NPD6411 Approved
0.5833 Remote Similarity NPD4758 Discontinued
0.5818 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5816 Remote Similarity NPD5210 Approved
0.5816 Remote Similarity NPD4629 Approved
0.581 Remote Similarity NPD6011 Approved
0.581 Remote Similarity NPD4730 Approved
0.581 Remote Similarity NPD5128 Approved
0.581 Remote Similarity NPD5168 Approved
0.581 Remote Similarity NPD4729 Approved
0.5806 Remote Similarity NPD4138 Approved
0.5806 Remote Similarity NPD4688 Approved
0.5806 Remote Similarity NPD4689 Approved
0.5806 Remote Similarity NPD5205 Approved
0.5806 Remote Similarity NPD4519 Discontinued
0.5806 Remote Similarity NPD4690 Approved
0.5806 Remote Similarity NPD4623 Approved
0.5806 Remote Similarity NPD4693 Phase 3
0.5804 Remote Similarity NPD8294 Approved
0.5804 Remote Similarity NPD8377 Approved
0.5802 Remote Similarity NPD4224 Phase 2
0.5794 Remote Similarity NPD6869 Approved
0.5794 Remote Similarity NPD6649 Approved
0.5794 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5794 Remote Similarity NPD6617 Approved
0.5794 Remote Similarity NPD6847 Approved
0.5794 Remote Similarity NPD8130 Phase 1
0.5794 Remote Similarity NPD6650 Approved
0.5789 Remote Similarity NPD6051 Approved
0.5789 Remote Similarity NPD8328 Phase 3
0.5773 Remote Similarity NPD8171 Discontinued
0.5769 Remote Similarity NPD1145 Discontinued
0.5766 Remote Similarity NPD7328 Approved
0.5766 Remote Similarity NPD7327 Approved
0.5758 Remote Similarity NPD7614 Phase 1
0.5755 Remote Similarity NPD6012 Approved
0.5755 Remote Similarity NPD6013 Approved
0.5755 Remote Similarity NPD6014 Approved
0.5752 Remote Similarity NPD8378 Approved
0.5752 Remote Similarity NPD8380 Approved
0.5752 Remote Similarity NPD8379 Approved
0.5752 Remote Similarity NPD8296 Approved
0.5752 Remote Similarity NPD8033 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