NPASS Compound

Structure

NPC206967 OpenBabel07101718242D 32 36 0 0 1 0 0 0 0 0999 V2000 -5.9333 -0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5008 0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3957 0.8889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1078 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1078 0.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9873 -0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4738 -1.1988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2652 -0.6723 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2652 1.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 -1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.9730 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 1.9459 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0143 -0.3561 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8426 1.4595 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9254 -1.2736 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4468 -1.1988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.9730 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.4226 -0.1858 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4973 -0.4865 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4226 0.7872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6852 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5279 1.4595 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9254 0.3007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9333 -2.0414 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5279 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8426 0.4865 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.4973 1.0878 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.3705 1.9459 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9062 -2.0414 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4468 -2.8840 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 17 1 0 0 0 0 3 27 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 8 1 0 0 0 0 7 14 1 0 0 0 0 8 17 2 0 0 0 0 9 19 2 0 0 0 0 10 21 2 0 0 0 0 11 12 1 0 0 0 0 11 18 1 0 0 0 0 12 22 1 0 0 0 0 13 15 1 0 0 0 0 13 23 1 0 0 0 0 14 26 1 0 0 0 0 15 27 1 0 0 0 0 16 18 1 0 0 0 0 16 20 1 0 0 0 0 17 25 1 0 0 0 0 18 28 1 6 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 24 2 0 0 0 0 21 29 1 0 0 0 0 22 26 1 1 0 0 0 22 27 1 0 0 0 0 23 26 1 1 0 0 0 23 30 1 0 0 0 0 24 28 1 0 0 0 0 24 29 1 0 0 0 0 25 31 2 0 0 0 0 25 32 1 0 0 0 0 26 2 1 1 0 0 0 27 28 1 6 0 0 0 28 4 1 6 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	435.28
Volume:	471.61
LogP:	5.704
LogD:	4.16
LogS:	-3.156
# Rotatable Bonds:	4
TPSA:	73.32
# H-Bond Aceptor:	4
# H-Bond Donor:	3
# Rings:	5
# Heavy Atoms:	4

MedChem Properties

QED Drug-Likeness Score:	0.517
Synthetic Accessibility Score:	4.428
Fsp3:	0.607
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.183
MDCK Permeability:	2.6883883037953638e-05
Pgp-inhibitor:	0.961
Pgp-substrate:	0.667
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.782
30% Bioavailability (F30%):	0.259

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.387
Plasma Protein Binding (PPB):	95.44660186767578%
Volume Distribution (VD):	0.25
Pgp-substrate:	4.1624979972839355%

ADMET: Metabolism

CYP1A2-inhibitor:	0.2
CYP1A2-substrate:	0.683
CYP2C19-inhibitor:	0.069
CYP2C19-substrate:	0.508
CYP2C9-inhibitor:	0.298
CYP2C9-substrate:	0.185
CYP2D6-inhibitor:	0.357
CYP2D6-substrate:	0.231
CYP3A4-inhibitor:	0.609
CYP3A4-substrate:	0.23

ADMET: Excretion

Clearance (CL):	6.875
Half-life (T1/2):	0.273

ADMET: Toxicity

hERG Blockers:	0.363
Human Hepatotoxicity (H-HT):	0.699
Drug-inuced Liver Injury (DILI):	0.032
AMES Toxicity:	0.003
Rat Oral Acute Toxicity:	0.922
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.932
Carcinogencity:	0.634
Eye Corrosion:	0.007
Eye Irritation:	0.036
Respiratory Toxicity:	0.977

Download Data

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

Natural Product: NPC206967

Natural Product ID:	NPC206967
*Common Name:**	Nodulisporic Acid F
IUPAC Name:	n.a.
Synonyms:	Nodulisporic Acid F
Standard InCHIKey:	FYZYVTHTMPXJHJ-UOOBVZAFSA-N
Standard InCHI:	InChI=1S/C28H37NO3/c1-17(25(31)32)8-7-14-26(2)22-12-11-18-16-20-19-9-5-6-10-21(19)29-24(20)28(18,4)27(22,3)15-13-23(26)30/h5-6,8-10,18,22-23,29-30H,7,11-16H2,1-4H3,(H,31,32)/b17-8+/t18-,22-,23-,26-,27-,28+/m0/s1
SMILES:	C/C(=CCC[C@@]1(C)[C@@H]2CC[C@H]3Cc4c5ccccc5[nH]c4[C@]3(C)[C@@]2(C)CC[C@@H]1O)/C(=O)O
Synthetic Gene Cluster:	BGC0001706;
ChEMBL Identifier:	CHEMBL458267
PubChem CID:	11281984
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001551] Diterpenoids

*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
NPO32628	nodulisporium	Genus	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15387649]

☑ 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
Others	1

Activity Type	# Activity
Organism	1
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2523	Organism	Ctenocephalides felis	Ctenocephalides felis	LD90	=	45.9	uM	PMID[509982]
NPT2	Others	Unspecified		IC50	>	10000.0	nM	PMID[509982]

☑ 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 NPC206967 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	267
0.1-0.2	1256
0.2-0.3	3761
0.3-0.4	19434
0.4-0.5	12915
0.5-0.6	3048
0.6-0.7	1662
0.7-0.8	295
0.8-0.85	33
0.85-0.9	20
0.9-0.95	4
0.95-1	2

Similarity Score	Similarity Level	Natural Product ID
0.9489	High Similarity	NPC473747
0.9408	High Similarity	NPC198339
0.9274	High Similarity	NPC475151
0.9226	High Similarity	NPC97525
0.8984	High Similarity	NPC250129
0.893	High Similarity	NPC475165
0.8908	High Similarity	NPC302191
0.8807	High Similarity	NPC165201
0.8793	High Similarity	NPC6093
0.8764	High Similarity	NPC119700
0.8717	High Similarity	NPC187456
0.8715	High Similarity	NPC34271
0.8656	High Similarity	NPC123019
0.8646	High Similarity	NPC97388
0.8603	High Similarity	NPC99428
0.8594	High Similarity	NPC473547
0.8519	High Similarity	NPC18661
0.8454	Intermediate Similarity	NPC471284
0.8454	Intermediate Similarity	NPC160527
0.8454	Intermediate Similarity	NPC473650
0.8446	Intermediate Similarity	NPC235900
0.8432	Intermediate Similarity	NPC231342
0.8391	Intermediate Similarity	NPC154293
0.8385	Intermediate Similarity	NPC284102
0.8378	Intermediate Similarity	NPC181502
0.8378	Intermediate Similarity	NPC85066
0.8324	Intermediate Similarity	NPC300688
0.8274	Intermediate Similarity	NPC96131
0.8192	Intermediate Similarity	NPC126492
0.8191	Intermediate Similarity	NPC242446
0.8191	Intermediate Similarity	NPC475476
0.8138	Intermediate Similarity	NPC205403
0.806	Intermediate Similarity	NPC61813
0.8011	Intermediate Similarity	NPC151939
0.7951	Intermediate Similarity	NPC79107
0.7951	Intermediate Similarity	NPC475424
0.7946	Intermediate Similarity	NPC476319
0.7944	Intermediate Similarity	NPC34508
0.7877	Intermediate Similarity	NPC201700
0.7869	Intermediate Similarity	NPC213468
0.7865	Intermediate Similarity	NPC477041
0.7865	Intermediate Similarity	NPC477044
0.7861	Intermediate Similarity	NPC204491
0.7861	Intermediate Similarity	NPC203614
0.7846	Intermediate Similarity	NPC98715
0.7835	Intermediate Similarity	NPC300183
0.7824	Intermediate Similarity	NPC477045
0.7816	Intermediate Similarity	NPC235885
0.7799	Intermediate Similarity	NPC282033
0.7784	Intermediate Similarity	NPC195461
0.7784	Intermediate Similarity	NPC81654
0.7784	Intermediate Similarity	NPC313985
0.7784	Intermediate Similarity	NPC249150
0.7784	Intermediate Similarity	NPC49196
0.7784	Intermediate Similarity	NPC79129
0.7778	Intermediate Similarity	NPC127677
0.7778	Intermediate Similarity	NPC258062
0.7772	Intermediate Similarity	NPC50503
0.7772	Intermediate Similarity	NPC270009
0.7754	Intermediate Similarity	NPC280290
0.775	Intermediate Similarity	NPC204303
0.7742	Intermediate Similarity	NPC19679
0.7727	Intermediate Similarity	NPC225821
0.7727	Intermediate Similarity	NPC46225
0.7688	Intermediate Similarity	NPC470280
0.7688	Intermediate Similarity	NPC192270
0.767	Intermediate Similarity	NPC470507
0.7665	Intermediate Similarity	NPC477135
0.765	Intermediate Similarity	NPC271862
0.7633	Intermediate Similarity	NPC469312
0.7633	Intermediate Similarity	NPC41318
0.7632	Intermediate Similarity	NPC46413
0.7626	Intermediate Similarity	NPC477043
0.7624	Intermediate Similarity	NPC151976
0.7624	Intermediate Similarity	NPC87856
0.7622	Intermediate Similarity	NPC293472
0.7616	Intermediate Similarity	NPC242556
0.76	Intermediate Similarity	NPC61637
0.7598	Intermediate Similarity	NPC132211
0.7596	Intermediate Similarity	NPC147446
0.7586	Intermediate Similarity	NPC267965
0.7585	Intermediate Similarity	NPC2395
0.7583	Intermediate Similarity	NPC471634
0.7583	Intermediate Similarity	NPC473806
0.7581	Intermediate Similarity	NPC472443
0.7577	Intermediate Similarity	NPC11445
0.7571	Intermediate Similarity	NPC471458
0.756	Intermediate Similarity	NPC141428
0.7558	Intermediate Similarity	NPC94541
0.7558	Intermediate Similarity	NPC470843
0.7553	Intermediate Similarity	NPC472444
0.7543	Intermediate Similarity	NPC124005
0.7543	Intermediate Similarity	NPC37548
0.7528	Intermediate Similarity	NPC285469
0.7528	Intermediate Similarity	NPC184476
0.7526	Intermediate Similarity	NPC157828
0.7526	Intermediate Similarity	NPC195239
0.7525	Intermediate Similarity	NPC234999
0.7514	Intermediate Similarity	NPC329688
0.7514	Intermediate Similarity	NPC189812
0.7513	Intermediate Similarity	NPC67551
0.75	Intermediate Similarity	NPC473320
0.75	Intermediate Similarity	NPC6982
0.7488	Intermediate Similarity	NPC57690
0.7476	Intermediate Similarity	NPC245756
0.7473	Intermediate Similarity	NPC470508
0.7472	Intermediate Similarity	NPC38736
0.7462	Intermediate Similarity	NPC476175
0.7459	Intermediate Similarity	NPC16667
0.7457	Intermediate Similarity	NPC311330
0.7446	Intermediate Similarity	NPC280548
0.7443	Intermediate Similarity	NPC187951
0.7438	Intermediate Similarity	NPC475422
0.7432	Intermediate Similarity	NPC470509
0.7429	Intermediate Similarity	NPC129042
0.7419	Intermediate Similarity	NPC472586
0.7418	Intermediate Similarity	NPC311276
0.7418	Intermediate Similarity	NPC40779
0.7418	Intermediate Similarity	NPC8104
0.7406	Intermediate Similarity	NPC183426
0.7389	Intermediate Similarity	NPC299594
0.7389	Intermediate Similarity	NPC469762
0.7386	Intermediate Similarity	NPC477134
0.738	Intermediate Similarity	NPC288785
0.7374	Intermediate Similarity	NPC207726
0.7374	Intermediate Similarity	NPC32200
0.7366	Intermediate Similarity	NPC475778
0.7358	Intermediate Similarity	NPC175474
0.735	Intermediate Similarity	NPC193761
0.7348	Intermediate Similarity	NPC67056
0.7344	Intermediate Similarity	NPC160381
0.734	Intermediate Similarity	NPC87755
0.7333	Intermediate Similarity	NPC469785
0.7333	Intermediate Similarity	NPC47190
0.7323	Intermediate Similarity	NPC52557
0.7322	Intermediate Similarity	NPC271734
0.7322	Intermediate Similarity	NPC472587
0.732	Intermediate Similarity	NPC95783
0.732	Intermediate Similarity	NPC469497
0.732	Intermediate Similarity	NPC106833
0.732	Intermediate Similarity	NPC329858
0.7313	Intermediate Similarity	NPC165599
0.7313	Intermediate Similarity	NPC476115
0.7302	Intermediate Similarity	NPC176199
0.7302	Intermediate Similarity	NPC215795
0.7291	Intermediate Similarity	NPC474905
0.7277	Intermediate Similarity	NPC112547
0.7277	Intermediate Similarity	NPC139291
0.7277	Intermediate Similarity	NPC267926
0.7277	Intermediate Similarity	NPC472108
0.7273	Intermediate Similarity	NPC472123
0.7268	Intermediate Similarity	NPC128751
0.7268	Intermediate Similarity	NPC214106
0.7268	Intermediate Similarity	NPC63199
0.7268	Intermediate Similarity	NPC111602
0.7268	Intermediate Similarity	NPC196251
0.7268	Intermediate Similarity	NPC102338
0.7264	Intermediate Similarity	NPC266192
0.7245	Intermediate Similarity	NPC55493
0.724	Intermediate Similarity	NPC190007
0.7233	Intermediate Similarity	NPC9894
0.7232	Intermediate Similarity	NPC212799
0.7231	Intermediate Similarity	NPC314333
0.7222	Intermediate Similarity	NPC469763
0.7222	Intermediate Similarity	NPC259644
0.7222	Intermediate Similarity	NPC469786
0.7222	Intermediate Similarity	NPC200743
0.7222	Intermediate Similarity	NPC469760
0.7222	Intermediate Similarity	NPC73952
0.7222	Intermediate Similarity	NPC469765
0.7222	Intermediate Similarity	NPC25008
0.7208	Intermediate Similarity	NPC474177
0.7206	Intermediate Similarity	NPC323927
0.7204	Intermediate Similarity	NPC317430
0.7204	Intermediate Similarity	NPC470874
0.7204	Intermediate Similarity	NPC78020
0.7202	Intermediate Similarity	NPC94943
0.72	Intermediate Similarity	NPC241024
0.7198	Intermediate Similarity	NPC12344
0.7194	Intermediate Similarity	NPC243716
0.7188	Intermediate Similarity	NPC469358
0.7184	Intermediate Similarity	NPC303951
0.7182	Intermediate Similarity	NPC80597
0.7182	Intermediate Similarity	NPC211572
0.7182	Intermediate Similarity	NPC75540
0.7182	Intermediate Similarity	NPC212376
0.7182	Intermediate Similarity	NPC70922
0.7181	Intermediate Similarity	NPC313791
0.7179	Intermediate Similarity	NPC246700
0.7178	Intermediate Similarity	NPC476874
0.7178	Intermediate Similarity	NPC162730
0.7178	Intermediate Similarity	NPC474116
0.7177	Intermediate Similarity	NPC330009
0.7177	Intermediate Similarity	NPC469928
0.7176	Intermediate Similarity	NPC475450
0.7172	Intermediate Similarity	NPC133366
0.7172	Intermediate Similarity	NPC19692
0.7172	Intermediate Similarity	NPC220151
0.7171	Intermediate Similarity	NPC39679
0.7165	Intermediate Similarity	NPC315555

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 NPC206967 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	197
0.1-0.2	558
0.2-0.3	556
0.3-0.4	1634
0.4-0.5	3424
0.5-0.6	2158
0.6-0.7	577
0.7-0.8	45
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.7868	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7784	Intermediate Similarity	NPD4601	Approved
0.7784	Intermediate Similarity	NPD4600	Approved
0.7737	Intermediate Similarity	NPD6630	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7957	Phase 1
0.75	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD2844	Phase 3
0.7473	Intermediate Similarity	NPD5744	Clinical (unspecified phase)
0.7449	Intermediate Similarity	NPD5003	Discontinued
0.7401	Intermediate Similarity	NPD4462	Approved
0.7401	Intermediate Similarity	NPD4463	Approved
0.7299	Intermediate Similarity	NPD1592	Phase 3
0.7277	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD43	Approved
0.7273	Intermediate Similarity	NPD6182	Approved
0.7273	Intermediate Similarity	NPD6183	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD5897	Approved
0.7263	Intermediate Similarity	NPD5898	Approved
0.7263	Intermediate Similarity	NPD5899	Approved
0.7258	Intermediate Similarity	NPD1325	Approved
0.7258	Intermediate Similarity	NPD1326	Approved
0.7231	Intermediate Similarity	NPD4499	Approved
0.7228	Intermediate Similarity	NPD6176	Phase 1
0.7212	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7192	Intermediate Similarity	NPD5901	Discontinued
0.7173	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7166	Intermediate Similarity	NPD7474	Suspended
0.7143	Intermediate Similarity	NPD2564	Approved
0.7143	Intermediate Similarity	NPD2565	Phase 2
0.7129	Intermediate Similarity	NPD7707	Approved
0.7128	Intermediate Similarity	NPD6739	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8431	Approved
0.712	Intermediate Similarity	NPD4079	Approved
0.712	Intermediate Similarity	NPD4076	Approved
0.712	Intermediate Similarity	NPD5398	Clinical (unspecified phase)
0.7112	Intermediate Similarity	NPD5069	Clinical (unspecified phase)
0.7105	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7102	Intermediate Similarity	NPD5020	Approved
0.7101	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.709	Intermediate Similarity	NPD7418	Discontinued
0.7083	Intermediate Similarity	NPD6595	Phase 3
0.7081	Intermediate Similarity	NPD972	Clinical (unspecified phase)
0.7079	Intermediate Similarity	NPD4501	Approved
0.7079	Intermediate Similarity	NPD4500	Approved
0.7068	Intermediate Similarity	NPD3505	Approved
0.7068	Intermediate Similarity	NPD3506	Approved
0.7065	Intermediate Similarity	NPD53	Approved
0.7065	Intermediate Similarity	NPD7778	Approved
0.7065	Intermediate Similarity	NPD7777	Approved
0.7059	Intermediate Similarity	NPD4554	Clinical (unspecified phase)
0.7053	Intermediate Similarity	NPD482	Approved
0.7053	Intermediate Similarity	NPD5065	Approved
0.7043	Intermediate Similarity	NPD6635	Approved
0.7041	Intermediate Similarity	NPD4948	Discontinued
0.7041	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD8386	Phase 2
0.7021	Intermediate Similarity	NPD5021	Discontinued
0.7016	Intermediate Similarity	NPD2381	Approved
0.7016	Intermediate Similarity	NPD2380	Approved
0.7016	Intermediate Similarity	NPD2382	Approved
0.7016	Intermediate Similarity	NPD5501	Discontinued
0.701	Intermediate Similarity	NPD2092	Phase 2
0.701	Intermediate Similarity	NPD5596	Phase 2
0.701	Intermediate Similarity	NPD2094	Phase 2
0.701	Intermediate Similarity	NPD5721	Clinical (unspecified phase)
0.701	Intermediate Similarity	NPD2095	Phase 2
0.7005	Intermediate Similarity	NPD1534	Approved
0.7	Intermediate Similarity	NPD4112	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD7470	Discontinued
0.6984	Remote Similarity	NPD4184	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD2144	Approved
0.6978	Remote Similarity	NPD6158	Phase 2
0.6978	Remote Similarity	NPD6476	Clinical (unspecified phase)
0.6977	Remote Similarity	NPD6995	Phase 1
0.6976	Remote Similarity	NPD8072	Approved
0.6974	Remote Similarity	NPD2091	Phase 2
0.6974	Remote Similarity	NPD2096	Phase 2
0.6959	Remote Similarity	NPD3038	Discontinued
0.6957	Remote Similarity	NPD6026	Approved
0.6952	Remote Similarity	NPD5138	Approved
0.6952	Remote Similarity	NPD5140	Approved
0.6942	Remote Similarity	NPD8282	Approved
0.6942	Remote Similarity	NPD56	Approved
0.6942	Remote Similarity	NPD8283	Approved
0.6935	Remote Similarity	NPD5913	Phase 3
0.6935	Remote Similarity	NPD5912	Clinical (unspecified phase)
0.6931	Remote Similarity	NPD7948	Phase 1
0.6927	Remote Similarity	NPD5254	Discontinued
0.6923	Remote Similarity	NPD2509	Approved
0.6923	Remote Similarity	NPD8399	Phase 1
0.6923	Remote Similarity	NPD4345	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD8423	Phase 2
0.6923	Remote Similarity	NPD5522	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD2510	Approved
0.6923	Remote Similarity	NPD6376	Discontinued
0.6919	Remote Similarity	NPD7233	Approved
0.6919	Remote Similarity	NPD7234	Approved
0.6912	Remote Similarity	NPD8248	Clinical (unspecified phase)
0.6908	Remote Similarity	NPD4862	Clinical (unspecified phase)
0.6907	Remote Similarity	NPD5473	Discontinued
0.6905	Remote Similarity	NPD5936	Approved
0.6905	Remote Similarity	NPD5939	Approved
0.6893	Remote Similarity	NPD2920	Discontinued
0.6891	Remote Similarity	NPD6203	Clinical (unspecified phase)
0.6881	Remote Similarity	NPD6449	Clinical (unspecified phase)
0.6878	Remote Similarity	NPD4511	Phase 1
0.6875	Remote Similarity	NPD8322	Phase 2
0.6872	Remote Similarity	NPD4383	Clinical (unspecified phase)
0.6869	Remote Similarity	NPD7878	Phase 2
0.6863	Remote Similarity	NPD6249	Phase 2
0.6863	Remote Similarity	NPD7621	Clinical (unspecified phase)
0.6863	Remote Similarity	NPD6248	Phase 2
0.6863	Remote Similarity	NPD6661	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8115	Approved
0.686	Remote Similarity	NPD8114	Approved
0.6857	Remote Similarity	NPD4880	Discontinued
0.6857	Remote Similarity	NPD7825	Clinical (unspecified phase)
0.6856	Remote Similarity	NPD3417	Phase 1
0.6854	Remote Similarity	NPD3943	Clinical (unspecified phase)
0.6853	Remote Similarity	NPD6610	Clinical (unspecified phase)
0.6845	Remote Similarity	NPD8073	Approved
0.684	Remote Similarity	NPD8094	Discontinued
0.6839	Remote Similarity	NPD6375	Clinical (unspecified phase)
0.6839	Remote Similarity	NPD5104	Approved
0.6834	Remote Similarity	NPD4334	Discontinued
0.6831	Remote Similarity	NPD3833	Phase 3
0.6831	Remote Similarity	NPD3835	Phase 3
0.6828	Remote Similarity	NPD4669	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4671	Clinical (unspecified phase)
0.6828	Remote Similarity	NPD4670	Clinical (unspecified phase)
0.6825	Remote Similarity	NPD2915	Discontinued
0.6823	Remote Similarity	NPD750	Phase 2
0.6821	Remote Similarity	NPD6452	Discontinued
0.682	Remote Similarity	NPD6160	Clinical (unspecified phase)
0.6814	Remote Similarity	NPD7946	Pre-registration
0.6811	Remote Similarity	NPD5257	Clinical (unspecified phase)
0.6798	Remote Similarity	NPD5512	Phase 3
0.6794	Remote Similarity	NPD5429	Discontinued
0.6793	Remote Similarity	NPD2882	Phase 1
0.6792	Remote Similarity	NPD8093	Discontinued
0.6791	Remote Similarity	NPD1554	Clinical (unspecified phase)
0.6788	Remote Similarity	NPD4736	Clinical (unspecified phase)
0.6782	Remote Similarity	NPD5575	Clinical (unspecified phase)
0.678	Remote Similarity	NPD8396	Approved
0.678	Remote Similarity	NPD8395	Approved
0.6779	Remote Similarity	NPD6987	Phase 1
0.6779	Remote Similarity	NPD6138	Clinical (unspecified phase)
0.6778	Remote Similarity	NPD3525	Discontinued
0.6776	Remote Similarity	NPD3393	Approved
0.6776	Remote Similarity	NPD3394	Approved
0.6776	Remote Similarity	NPD3389	Approved
0.6768	Remote Similarity	NPD6344	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD5592	Clinical (unspecified phase)
0.6763	Remote Similarity	NPD7187	Phase 2
0.6762	Remote Similarity	NPD2916	Discontinued
0.6761	Remote Similarity	NPD7276	Approved
0.6761	Remote Similarity	NPD7277	Approved
0.6757	Remote Similarity	NPD7688	Phase 1
0.6754	Remote Similarity	NPD4638	Approved
0.6754	Remote Similarity	NPD4640	Approved
0.6754	Remote Similarity	NPD4639	Approved
0.6753	Remote Similarity	NPD4075	Phase 2
0.675	Remote Similarity	NPD8110	Clinical (unspecified phase)
0.6749	Remote Similarity	NPD7944	Discontinued
0.6748	Remote Similarity	NPD6479	Discontinued
0.6748	Remote Similarity	NPD484	Approved
0.6746	Remote Similarity	NPD2715	Clinical (unspecified phase)
0.6745	Remote Similarity	NPD8013	Clinical (unspecified phase)
0.6738	Remote Similarity	NPD4326	Phase 2
0.6733	Remote Similarity	NPD6619	Phase 3
0.6731	Remote Similarity	NPD2121	Clinical (unspecified phase)
0.673	Remote Similarity	NPD7941	Phase 3
0.673	Remote Similarity	NPD4506	Discontinued
0.6718	Remote Similarity	NPD7865	Approved
0.6717	Remote Similarity	NPD3607	Clinical (unspecified phase)
0.6716	Remote Similarity	NPD6281	Approved
0.6715	Remote Similarity	NPD7931	Approved
0.6715	Remote Similarity	NPD7932	Clinical (unspecified phase)
0.6715	Remote Similarity	NPD7933	Approved
0.6715	Remote Similarity	NPD7934	Discovery
0.6714	Remote Similarity	NPD6657	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD8493	Clinical (unspecified phase)
0.6714	Remote Similarity	NPD6838	Clinical (unspecified phase)
0.6713	Remote Similarity	NPD8405	Clinical (unspecified phase)
0.6701	Remote Similarity	NPD6492	Phase 2
0.67	Remote Similarity	NPD3486	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD3800	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD6323	Clinical (unspecified phase)
0.6699	Remote Similarity	NPD2721	Clinical (unspecified phase)
0.6698	Remote Similarity	NPD8160	Phase 2
0.6685	Remote Similarity	NPD1262	Discovery
0.6684	Remote Similarity	NPD3323	Discontinued
0.6683	Remote Similarity	NPD3785	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD5164	Discontinued
0.6667	Remote Similarity	NPD7070	Clinical (unspecified phase)
0.6667	Remote Similarity	NPD3319	Phase 1
0.6667	Remote Similarity	NPD3320	Approved
0.6667	Remote Similarity	NPD3318	Approved
0.6667	Remote Similarity	NPD3791	Clinical (unspecified phase)
0.6651	Remote Similarity	NPD2125	Clinical (unspecified phase)

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