NPASS Compound

Structure

CID197682 OpenBabel06191715582D 70 71 0 0 1 0 0 0 0 0999 V2000 4.0900 -4.2300 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9290 -5.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8422 -9.6667 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3070 -11.3140 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2851 -4.1654 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1040 -5.8879 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0630 -8.2615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 -3.7653 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2979 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4538 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4456 1.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4456 1.2796 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4067 0.9135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -10.1532 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4459 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4459 -6.1570 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2979 -3.2518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9290 -6.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5522 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.5522 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6862 -3.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5547 -2.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.6862 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8202 -2.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1480 -10.0268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 -1.4781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -8.7397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5003 -7.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0991 -10.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6973 -4.9744 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0630 -7.2615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8116 -3.8698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8912 -0.0000 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 -7.8202 -1.9781 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 -2.8917 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.9401 -9.0487 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.0881 -1.9781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9511 -9.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0881 -6.7615 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7028 -4.8698 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1970 -6.7615 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.9401 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8912 -8.7397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5003 -1.1691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6092 -7.5706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7028 -3.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8116 -4.8698 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9511 0.3090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 0.4135 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7572 -8.2397 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -8.2397 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7572 -0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.1970 -1.9781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.9456 -9.1532 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.4948 -2.8917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.4948 -5.8480 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -10.0268 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 -7.2615 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1480 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2979 -9.6532 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.2435 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.3523 -8.2397 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.6973 -3.7653 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8061 -4.9744 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 1.2872 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 -5.8480 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 2 18 1 0 0 0 0 3 29 1 0 0 0 0 4 29 1 0 0 0 0 5 30 1 0 0 0 0 6 30 1 0 0 0 0 11 51 1 0 0 0 0 12 51 1 0 0 0 0 13 56 1 0 0 0 0 14 57 1 0 0 0 0 15 58 1 0 0 0 0 16 59 1 0 0 0 0 17 22 1 0 0 0 0 18 31 1 0 0 0 0 19 20 2 0 0 0 0 19 21 1 0 0 0 0 20 23 1 0 0 0 0 21 24 2 0 0 0 0 23 35 2 0 0 0 0 24 35 1 0 0 0 0 25 29 1 0 0 0 0 26 35 1 0 0 0 0 27 39 1 0 0 0 0 27 53 1 0 0 0 0 28 40 1 0 0 0 0 28 52 1 0 0 0 0 31 7 1 6 0 0 0 32 8 1 6 0 0 0 32 36 1 0 0 0 0 32 49 1 0 0 0 0 33 9 1 1 0 0 0 33 43 1 0 0 0 0 33 54 1 0 0 0 0 34 10 1 1 0 0 0 34 44 1 0 0 0 0 34 56 1 0 0 0 0 36 22 1 6 0 0 0 36 55 1 0 0 0 0 37 25 1 1 0 0 0 37 45 1 0 0 0 0 37 57 1 0 0 0 0 38 26 1 1 0 0 0 38 46 1 0 0 0 0 38 58 1 0 0 0 0 39 57 1 0 0 0 0 39 60 2 0 0 0 0 40 59 1 0 0 0 0 40 61 2 0 0 0 0 41 30 1 1 0 0 0 41 48 1 0 0 0 0 41 59 1 0 0 0 0 42 31 1 1 0 0 0 42 47 1 0 0 0 0 42 70 1 0 0 0 0 43 51 1 0 0 0 0 43 62 2 0 0 0 0 44 55 2 3 0 0 0 44 63 1 0 0 0 0 45 52 2 3 0 0 0 45 64 1 0 0 0 0 46 54 2 3 0 0 0 46 65 1 0 0 0 0 47 53 2 3 0 0 0 47 66 1 0 0 0 0 48 58 1 0 0 0 0 48 67 2 0 0 0 0 49 68 2 0 0 0 0 49 70 1 0 0 0 0 50 51 1 0 0 0 0 50 56 1 0 0 0 0 50 69 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	982.61
Volume:	1023.931
LogP:	3.608
LogD:	3.129
LogS:	-4.115
# Rotatable Bonds:	9
TPSA:	241.01
# H-Bond Aceptor:	19
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	19

MedChem Properties

QED Drug-Likeness Score:	0.207
Synthetic Accessibility Score:	6.315
Fsp3:	0.686
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:	-5.41
MDCK Permeability:	1.4612302038585767e-05
Pgp-inhibitor:	1.0
Pgp-substrate:	0.951
Human Intestinal Absorption (HIA):	0.876
20% Bioavailability (F20%):	0.03
30% Bioavailability (F30%):	0.738

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.044
Plasma Protein Binding (PPB):	82.58731842041016%
Volume Distribution (VD):	0.763
Pgp-substrate:	20.438709259033203%

ADMET: Metabolism

CYP1A2-inhibitor:	0.0
CYP1A2-substrate:	0.018
CYP2C19-inhibitor:	0.046
CYP2C19-substrate:	0.165
CYP2C9-inhibitor:	0.118
CYP2C9-substrate:	0.017
CYP2D6-inhibitor:	0.002
CYP2D6-substrate:	0.036
CYP3A4-inhibitor:	0.9
CYP3A4-substrate:	0.783

ADMET: Excretion

Clearance (CL):	6.249
Half-life (T1/2):	0.105

ADMET: Toxicity

hERG Blockers:	0.002
Human Hepatotoxicity (H-HT):	0.967
Drug-inuced Liver Injury (DILI):	0.938
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.219
Maximum Recommended Daily Dose:	0.088
Skin Sensitization:	0.191
Carcinogencity:	0.013
Eye Corrosion:	0.003
Eye Irritation:	0.004
Respiratory Toxicity:	0.384

Download Data

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

Natural Product: NPC197682

Natural Product ID:	NPC197682
*Common Name:**	Ibu-Epidemethoxylyngbyastatin 3
IUPAC Name:	(2S,8S,14S,17S,20S,25S,28R,29S)-17-benzyl-2-[(2S)-butan-2-yl]-7,13,16,20,22,22,24,25,29-nonamethyl-8-(2-methylpropyl)-14-propan-2-yl-28-propyl-1-oxa-4,7,10,13,16,19,24,27-octazacyclotriacontane-3,6,9,12,15,18,21,23,26,30-decone
Synonyms:	Ibu-Epidemethoxylyngbyastatin 3
Standard InCHIKey:	IIRHRPDTNGFOSK-ONMSWCRESA-N
Standard InCHI:	InChI=1S/C51H82N8O11/c1-17-22-36-32(8)49(68)70-42(31(7)18-2)47(66)53-27-39(60)57(14)37(25-29(3)4)45(64)52-28-40(61)59(16)41(30(5)6)48(67)58(15)38(26-35-23-20-19-21-24-35)46(65)54-33(9)43(62)51(11,12)50(69)56(13)34(10)44(63)55-36/h19-21,23-24,29-34,36-38,41-42H,17-18,22,25-28H2,1-16H3,(H,52,64)(H,53,66)(H,54,65)(H,55,63)/t31-,32-,33-,34-,36+,37-,38-,41-,42-/m0/s1
SMILES:	CCC[C@H]1N=C(O)[C@H](C)N(C)C(=O)C(C)(C)C(=O)[C@H](C)N=C(O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H](C(C)C)N(C(=O)CN=C([C@@H](N(C(=O)CN=C([C@@H](OC(=O)[C@H]1C)[C@H](CC)C)O)C)CC(C)C)O)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1823871
PubChem CID:	53492935
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0001813] Peptidomimetics [CHEMONTID:0001961] Depsipeptides [CHEMONTID:0001994] Cyclic depsipeptides

*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
NPO31131	Leptolyngbya species	Species	Leptolyngbyaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21806012]

☑ 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
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[506581]

☑ 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 NPC197682 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	132
0.1-0.2	655
0.2-0.3	3118
0.3-0.4	18468
0.4-0.5	16904
0.5-0.6	2574
0.6-0.7	511
0.7-0.8	259
0.8-0.85	66
0.85-0.9	6
0.9-0.95	1
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9924	High Similarity	NPC168113
0.9552	High Similarity	NPC176226
0.9259	High Similarity	NPC476259
0.8832	High Similarity	NPC127741
0.8832	High Similarity	NPC68865
0.8582	High Similarity	NPC139326
0.8571	High Similarity	NPC307357
0.8571	High Similarity	NPC46098
0.8571	High Similarity	NPC268841
0.8511	High Similarity	NPC269398
0.8511	High Similarity	NPC263493
0.8497	Intermediate Similarity	NPC186617
0.8472	Intermediate Similarity	NPC135121
0.8462	Intermediate Similarity	NPC477217
0.8462	Intermediate Similarity	NPC5620
0.8462	Intermediate Similarity	NPC201244
0.8451	Intermediate Similarity	NPC161069
0.8429	Intermediate Similarity	NPC471264
0.8429	Intermediate Similarity	NPC471265
0.8382	Intermediate Similarity	NPC319766
0.8369	Intermediate Similarity	NPC470884
0.8369	Intermediate Similarity	NPC476133
0.8369	Intermediate Similarity	NPC92784
0.8369	Intermediate Similarity	NPC178662
0.8369	Intermediate Similarity	NPC98424
0.8356	Intermediate Similarity	NPC2501
0.8345	Intermediate Similarity	NPC145113
0.8333	Intermediate Similarity	NPC209509
0.8333	Intermediate Similarity	NPC297145
0.8333	Intermediate Similarity	NPC197743
0.831	Intermediate Similarity	NPC239762
0.831	Intermediate Similarity	NPC163392
0.8276	Intermediate Similarity	NPC262077
0.8264	Intermediate Similarity	NPC52748
0.8264	Intermediate Similarity	NPC476978
0.8258	Intermediate Similarity	NPC237420
0.8252	Intermediate Similarity	NPC469427
0.8252	Intermediate Similarity	NPC469426
0.8243	Intermediate Similarity	NPC162104
0.8231	Intermediate Similarity	NPC129666
0.8219	Intermediate Similarity	NPC138775
0.8205	Intermediate Similarity	NPC473693
0.8205	Intermediate Similarity	NPC471568
0.8188	Intermediate Similarity	NPC122590
0.8163	Intermediate Similarity	NPC471820
0.8163	Intermediate Similarity	NPC105717
0.8163	Intermediate Similarity	NPC471821
0.8082	Intermediate Similarity	NPC315266
0.8014	Intermediate Similarity	NPC246079
0.7987	Intermediate Similarity	NPC471527
0.7985	Intermediate Similarity	NPC470546
0.7973	Intermediate Similarity	NPC329761
0.7973	Intermediate Similarity	NPC225648
0.7959	Intermediate Similarity	NPC313867
0.7959	Intermediate Similarity	NPC316008
0.7958	Intermediate Similarity	NPC287401
0.7947	Intermediate Similarity	NPC286551
0.7922	Intermediate Similarity	NPC1390
0.7922	Intermediate Similarity	NPC62104
0.7919	Intermediate Similarity	NPC240848
0.791	Intermediate Similarity	NPC470545
0.791	Intermediate Similarity	NPC169328
0.7905	Intermediate Similarity	NPC314358
0.7891	Intermediate Similarity	NPC315283
0.7891	Intermediate Similarity	NPC314388
0.7885	Intermediate Similarity	NPC471052
0.7885	Intermediate Similarity	NPC471051
0.7885	Intermediate Similarity	NPC471053
0.7852	Intermediate Similarity	NPC310467
0.7842	Intermediate Similarity	NPC101719
0.7836	Intermediate Similarity	NPC470544
0.7829	Intermediate Similarity	NPC473341
0.7826	Intermediate Similarity	NPC46427
0.7826	Intermediate Similarity	NPC6975
0.7817	Intermediate Similarity	NPC130309
0.7778	Intermediate Similarity	NPC248283
0.777	Intermediate Similarity	NPC222466
0.7754	Intermediate Similarity	NPC252878
0.774	Intermediate Similarity	NPC132636
0.7737	Intermediate Similarity	NPC200964
0.7722	Intermediate Similarity	NPC210377
0.7722	Intermediate Similarity	NPC5719
0.7722	Intermediate Similarity	NPC217804
0.7722	Intermediate Similarity	NPC22883
0.7718	Intermediate Similarity	NPC322878
0.7704	Intermediate Similarity	NPC239357
0.7697	Intermediate Similarity	NPC475168
0.7697	Intermediate Similarity	NPC7817
0.7692	Intermediate Similarity	NPC255447
0.7681	Intermediate Similarity	NPC202521
0.7676	Intermediate Similarity	NPC473322
0.7673	Intermediate Similarity	NPC15068
0.7625	Intermediate Similarity	NPC63040
0.7609	Intermediate Similarity	NPC478015
0.7609	Intermediate Similarity	NPC476990
0.7609	Intermediate Similarity	NPC478016
0.7609	Intermediate Similarity	NPC478014
0.7607	Intermediate Similarity	NPC477462
0.7607	Intermediate Similarity	NPC26108
0.7606	Intermediate Similarity	NPC105114
0.7606	Intermediate Similarity	NPC89923
0.7606	Intermediate Similarity	NPC239990
0.7606	Intermediate Similarity	NPC152850
0.7606	Intermediate Similarity	NPC71933
0.7591	Intermediate Similarity	NPC314992
0.7589	Intermediate Similarity	NPC47667
0.7554	Intermediate Similarity	NPC71684
0.7548	Intermediate Similarity	NPC470902
0.7546	Intermediate Similarity	NPC248670
0.7535	Intermediate Similarity	NPC136453
0.7532	Intermediate Similarity	NPC300443
0.7531	Intermediate Similarity	NPC196091
0.7518	Intermediate Similarity	NPC22746
0.75	Intermediate Similarity	NPC300315
0.7482	Intermediate Similarity	NPC45777
0.7482	Intermediate Similarity	NPC477061
0.7481	Intermediate Similarity	NPC276949
0.7481	Intermediate Similarity	NPC35850
0.7455	Intermediate Similarity	NPC50016
0.7448	Intermediate Similarity	NPC157311
0.7447	Intermediate Similarity	NPC35996
0.7445	Intermediate Similarity	NPC2265
0.7434	Intermediate Similarity	NPC81026
0.7431	Intermediate Similarity	NPC111428
0.7426	Intermediate Similarity	NPC33742
0.7397	Intermediate Similarity	NPC44805
0.7397	Intermediate Similarity	NPC8761
0.7394	Intermediate Similarity	NPC318930
0.7394	Intermediate Similarity	NPC476241
0.7394	Intermediate Similarity	NPC473354
0.7394	Intermediate Similarity	NPC471165
0.7394	Intermediate Similarity	NPC317725
0.7394	Intermediate Similarity	NPC326407
0.7394	Intermediate Similarity	NPC476260
0.7394	Intermediate Similarity	NPC317362
0.7391	Intermediate Similarity	NPC63931
0.7375	Intermediate Similarity	NPC73655
0.7368	Intermediate Similarity	NPC266741
0.7357	Intermediate Similarity	NPC190663
0.7351	Intermediate Similarity	NPC77905
0.7343	Intermediate Similarity	NPC476125
0.7343	Intermediate Similarity	NPC476179
0.7333	Intermediate Similarity	NPC273755
0.7325	Intermediate Similarity	NPC39431
0.7324	Intermediate Similarity	NPC175726
0.7324	Intermediate Similarity	NPC474082
0.7317	Intermediate Similarity	NPC40234
0.7317	Intermediate Similarity	NPC475123
0.7317	Intermediate Similarity	NPC475204
0.7317	Intermediate Similarity	NPC46009
0.7315	Intermediate Similarity	NPC6570
0.7315	Intermediate Similarity	NPC43755
0.7312	Intermediate Similarity	NPC469901
0.731	Intermediate Similarity	NPC469666
0.7301	Intermediate Similarity	NPC107938
0.7301	Intermediate Similarity	NPC294516
0.7301	Intermediate Similarity	NPC473502
0.7289	Intermediate Similarity	NPC476227
0.7284	Intermediate Similarity	NPC472923
0.7279	Intermediate Similarity	NPC474584
0.7273	Intermediate Similarity	NPC89831
0.7262	Intermediate Similarity	NPC45037
0.726	Intermediate Similarity	NPC200589
0.7256	Intermediate Similarity	NPC473000
0.7254	Intermediate Similarity	NPC160493
0.725	Intermediate Similarity	NPC24617
0.7234	Intermediate Similarity	NPC476183
0.7229	Intermediate Similarity	NPC306804
0.7229	Intermediate Similarity	NPC137627
0.7205	Intermediate Similarity	NPC114806
0.7195	Intermediate Similarity	NPC209463
0.7193	Intermediate Similarity	NPC471049
0.7193	Intermediate Similarity	NPC471048
0.7193	Intermediate Similarity	NPC294951
0.7193	Intermediate Similarity	NPC471050
0.7186	Intermediate Similarity	NPC159767
0.7186	Intermediate Similarity	NPC473402
0.7186	Intermediate Similarity	NPC155506
0.7186	Intermediate Similarity	NPC279871
0.7183	Intermediate Similarity	NPC476184
0.7183	Intermediate Similarity	NPC476281
0.7181	Intermediate Similarity	NPC141050
0.7179	Intermediate Similarity	NPC283783
0.7176	Intermediate Similarity	NPC476321
0.717	Intermediate Similarity	NPC469903
0.7169	Intermediate Similarity	NPC230611
0.716	Intermediate Similarity	NPC475421
0.7153	Intermediate Similarity	NPC273814
0.7143	Intermediate Similarity	NPC469898
0.7135	Intermediate Similarity	NPC471526
0.7134	Intermediate Similarity	NPC324081
0.7122	Intermediate Similarity	NPC197470
0.7113	Intermediate Similarity	NPC80150
0.7083	Intermediate Similarity	NPC476278
0.7081	Intermediate Similarity	NPC324850
0.7075	Intermediate Similarity	NPC213969
0.7075	Intermediate Similarity	NPC165726
0.7071	Intermediate Similarity	NPC14672
0.7071	Intermediate Similarity	NPC285926
0.7071	Intermediate Similarity	NPC315276

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 NPC197682 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	99
0.1-0.2	317
0.2-0.3	743
0.3-0.4	2524
0.4-0.5	3770
0.5-0.6	1345
0.6-0.7	321
0.7-0.8	31
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8042	Intermediate Similarity	NPD8172	Phase 2
0.8042	Intermediate Similarity	NPD8173	Phase 2
0.8028	Intermediate Similarity	NPD8416	Discontinued
0.7724	Intermediate Similarity	NPD8643	Discontinued
0.7724	Intermediate Similarity	NPD7113	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD8076	Discontinued
0.7698	Intermediate Similarity	NPD2584	Suspended
0.7619	Intermediate Similarity	NPD6852	Discontinued
0.7616	Intermediate Similarity	NPD8323	Discontinued
0.7591	Intermediate Similarity	NPD2218	Phase 2
0.7591	Intermediate Similarity	NPD2217	Approved
0.7569	Intermediate Similarity	NPD6919	Clinical (unspecified phase)
0.7552	Intermediate Similarity	NPD3626	Phase 3
0.75	Intermediate Similarity	NPD6901	Phase 3
0.7483	Intermediate Similarity	NPD3608	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD8417	Discontinued
0.7413	Intermediate Similarity	NPD2585	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD4175	Approved
0.731	Intermediate Similarity	NPD4177	Approved
0.7303	Intermediate Similarity	NPD6681	Discovery
0.7297	Intermediate Similarity	NPD4153	Approved
0.7286	Intermediate Similarity	NPD4504	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD4125	Approved
0.7241	Intermediate Similarity	NPD5339	Clinical (unspecified phase)
0.7237	Intermediate Similarity	NPD4152	Approved
0.7211	Intermediate Similarity	NPD4738	Phase 2
0.72	Intermediate Similarity	NPD6073	Approved
0.72	Intermediate Similarity	NPD5725	Approved
0.719	Intermediate Similarity	NPD6119	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD7749	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD8265	Approved
0.7181	Intermediate Similarity	NPD6623	Phase 3
0.7179	Intermediate Similarity	NPD6088	Approved
0.7179	Intermediate Similarity	NPD7892	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD4677	Discontinued
0.7122	Intermediate Similarity	NPD1348	Approved
0.7114	Intermediate Similarity	NPD3561	Clinical (unspecified phase)
0.7099	Intermediate Similarity	NPD7599	Phase 2
0.7099	Intermediate Similarity	NPD4557	Approved
0.7083	Intermediate Similarity	NPD3073	Approved
0.7083	Intermediate Similarity	NPD3072	Approved
0.7083	Intermediate Similarity	NPD3071	Approved
0.7075	Intermediate Similarity	NPD3040	Approved
0.7055	Intermediate Similarity	NPD7600	Phase 2
0.7039	Intermediate Similarity	NPD6295	Approved
0.7039	Intermediate Similarity	NPD6294	Approved
0.7032	Intermediate Similarity	NPD6860	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD7979	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4706	Clinical (unspecified phase)
0.7014	Intermediate Similarity	NPD4761	Approved
0.7014	Intermediate Similarity	NPD4762	Approved
0.7013	Intermediate Similarity	NPD2022	Approved
0.7007	Intermediate Similarity	NPD3604	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5747	Discontinued
0.7	Intermediate Similarity	NPD7634	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD8315	Phase 1
0.6993	Remote Similarity	NPD7728	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD7342	Discontinued
0.6986	Remote Similarity	NPD5367	Discontinued
0.6986	Remote Similarity	NPD3125	Approved
0.6981	Remote Similarity	NPD7613	Discontinued
0.698	Remote Similarity	NPD2045	Approved
0.698	Remote Similarity	NPD2051	Approved
0.698	Remote Similarity	NPD2047	Approved
0.698	Remote Similarity	NPD21	Approved
0.698	Remote Similarity	NPD2046	Approved
0.698	Remote Similarity	NPD2043	Approved
0.698	Remote Similarity	NPD2049	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2044	Approved
0.698	Remote Similarity	NPD2050	Clinical (unspecified phase)
0.698	Remote Similarity	NPD2048	Approved
0.6975	Remote Similarity	NPD7118	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD4782	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6631	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD5323	Approved
0.6954	Remote Similarity	NPD5296	Approved
0.6928	Remote Similarity	NPD8303	Discontinued
0.6923	Remote Similarity	NPD5981	Approved
0.6923	Remote Similarity	NPD8126	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8124	Phase 3
0.6913	Remote Similarity	NPD5263	Approved
0.6913	Remote Similarity	NPD4676	Approved
0.6903	Remote Similarity	NPD2087	Approved
0.6903	Remote Similarity	NPD2088	Approved
0.6903	Remote Similarity	NPD7720	Phase 2
0.6894	Remote Similarity	NPD4646	Approved
0.6894	Remote Similarity	NPD4647	Approved
0.6894	Remote Similarity	NPD4648	Approved
0.6884	Remote Similarity	NPD3643	Approved
0.6884	Remote Similarity	NPD3644	Approved
0.6884	Remote Similarity	NPD3642	Approved
0.6883	Remote Similarity	NPD3480	Approved
0.6883	Remote Similarity	NPD5301	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD5298	Clinical (unspecified phase)
0.6879	Remote Similarity	NPD1968	Approved
0.6879	Remote Similarity	NPD1967	Approved
0.6875	Remote Similarity	NPD5230	Approved
0.6875	Remote Similarity	NPD5229	Approved
0.6871	Remote Similarity	NPD6325	Discontinued
0.6859	Remote Similarity	NPD2437	Approved
0.6859	Remote Similarity	NPD2436	Approved
0.6849	Remote Similarity	NPD7814	Approved
0.6842	Remote Similarity	NPD4791	Clinical (unspecified phase)
0.6835	Remote Similarity	NPD6552	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD5581	Approved
0.6821	Remote Similarity	NPD1329	Clinical (unspecified phase)
0.6821	Remote Similarity	NPD1330	Phase 2
0.6821	Remote Similarity	NPD5299	Approved
0.681	Remote Similarity	NPD7267	Clinical (unspecified phase)
0.6805	Remote Similarity	NPD7608	Discontinued
0.679	Remote Similarity	NPD6670	Clinical (unspecified phase)
0.6786	Remote Similarity	NPD2607	Approved
0.6779	Remote Similarity	NPD3588	Discontinued
0.6776	Remote Similarity	NPD5729	Clinical (unspecified phase)
0.6755	Remote Similarity	NPD4794	Discontinued
0.675	Remote Similarity	NPD3987	Approved
0.675	Remote Similarity	NPD5613	Approved
0.675	Remote Similarity	NPD5614	Approved
0.675	Remote Similarity	NPD3988	Approved
0.6747	Remote Similarity	NPD7080	Clinical (unspecified phase)
0.6731	Remote Similarity	NPD7511	Approved
0.6731	Remote Similarity	NPD7512	Approved
0.6725	Remote Similarity	NPD7965	Phase 2
0.6725	Remote Similarity	NPD7964	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7130	Phase 3
0.6712	Remote Similarity	NPD7813	Approved
0.6712	Remote Similarity	NPD7815	Approved
0.6711	Remote Similarity	NPD2626	Approved
0.6711	Remote Similarity	NPD2625	Approved
0.6711	Remote Similarity	NPD2628	Approved
0.6711	Remote Similarity	NPD2160	Approved
0.6711	Remote Similarity	NPD2627	Approved
0.6711	Remote Similarity	NPD2159	Approved
0.671	Remote Similarity	NPD4214	Discontinued
0.6709	Remote Similarity	NPD5264	Approved
0.6709	Remote Similarity	NPD5265	Approved
0.6707	Remote Similarity	NPD8351	Phase 2
0.6707	Remote Similarity	NPD2891	Approved
0.6689	Remote Similarity	NPD2613	Approved
0.6687	Remote Similarity	NPD8290	Clinical (unspecified phase)
0.6687	Remote Similarity	NPD3519	Discontinued
0.6686	Remote Similarity	NPD4508	Discontinued
0.6667	Remote Similarity	NPD2612	Approved
0.6667	Remote Similarity	NPD2611	Approved
0.6667	Remote Similarity	NPD3131	Approved
0.6667	Remote Similarity	NPD2608	Approved
0.6667	Remote Similarity	NPD3132	Approved
0.6667	Remote Similarity	NPD8118	Discontinued
0.6667	Remote Similarity	NPD2610	Approved
0.6667	Remote Similarity	NPD4151	Approved
0.6667	Remote Similarity	NPD4216	Approved
0.6667	Remote Similarity	NPD2609	Approved
0.6667	Remote Similarity	NPD4218	Approved
0.6667	Remote Similarity	NPD4215	Approved
0.6667	Remote Similarity	NPD7522	Discontinued
0.6667	Remote Similarity	NPD4217	Approved
0.6647	Remote Similarity	NPD7485	Phase 3
0.6647	Remote Similarity	NPD7484	Phase 3
0.6646	Remote Similarity	NPD5341	Clinical (unspecified phase)
0.6644	Remote Similarity	NPD6792	Phase 3
0.6626	Remote Similarity	NPD7131	Phase 3
0.6625	Remote Similarity	NPD7602	Clinical (unspecified phase)
0.6624	Remote Similarity	NPD6897	Clinical (unspecified phase)
0.6623	Remote Similarity	NPD3662	Phase 3
0.6623	Remote Similarity	NPD7828	Discontinued
0.6623	Remote Similarity	NPD3664	Approved
0.6623	Remote Similarity	NPD5759	Approved
0.6623	Remote Similarity	NPD3663	Approved
0.6623	Remote Similarity	NPD3661	Approved
0.6622	Remote Similarity	NPD5108	Clinical (unspecified phase)
0.6621	Remote Similarity	NPD6343	Approved
0.6621	Remote Similarity	NPD6345	Approved
0.6609	Remote Similarity	NPD5681	Clinical (unspecified phase)
0.6605	Remote Similarity	NPD4682	Phase 2
0.6605	Remote Similarity	NPD4432	Discontinued
0.6605	Remote Similarity	NPD4185	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD3632	Clinical (unspecified phase)
0.6601	Remote Similarity	NPD7908	Discontinued
0.6601	Remote Similarity	NPD2078	Clinical (unspecified phase)
0.6597	Remote Similarity	NPD5292	Approved
0.6597	Remote Similarity	NPD3123	Discovery
0.6597	Remote Similarity	NPD5291	Approved
0.6582	Remote Similarity	NPD7978	Discontinued
0.6581	Remote Similarity	NPD4757	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD6359	Clinical (unspecified phase)
0.6579	Remote Similarity	NPD5202	Clinical (unspecified phase)
0.6571	Remote Similarity	NPD4234	Approved
0.6571	Remote Similarity	NPD4233	Approved
0.6566	Remote Similarity	NPD7105	Phase 1
0.6564	Remote Similarity	NPD6078	Clinical (unspecified phase)
0.6562	Remote Similarity	NPD6676	Phase 2
0.6561	Remote Similarity	NPD4158	Clinical (unspecified phase)
0.6558	Remote Similarity	NPD4745	Approved
0.6558	Remote Similarity	NPD2574	Discontinued
0.6558	Remote Similarity	NPD4746	Phase 3
0.6558	Remote Similarity	NPD3616	Approved
0.6558	Remote Similarity	NPD2571	Approved
0.6558	Remote Similarity	NPD3090	Approved
0.6558	Remote Similarity	NPD3087	Approved
0.6558	Remote Similarity	NPD3088	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