NPASS Compound

Natural Product: NPC211162

Natural Product ID	NPC211162
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Ceanothic Acid
IUPAC Name	n.a.
Synonyms	Ceanothic Acid
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL491069
PubChem CID	161352
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 81 85 0 0 0 0 0 0 0 0999 V2000 -3.4228 -3.1538 1.5848 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8012 -2.3400 0.6135 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0723 -2.8786 -0.7279 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.9411 -0.8757 0.9198 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.3262 -0.4730 0.3864 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0650 0.5234 -0.7553 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7839 1.1715 -0.2492 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0287 1.9411 -1.2378 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6763 1.5255 -1.6471 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9233 0.5840 -0.7652 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8429 -0.7509 -1.4649 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7089 0.3136 0.5371 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0077 -0.6157 1.4624 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3379 0.0381 1.8042 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0813 0.1190 0.5242 C 0 0 1 0 0 0 0 0 0 0 0 0 0.4703 1.1416 -0.4147 C 0 0 2 0 0 0 0 0 0 0 0 0 0.2607 2.4942 0.2077 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2204 1.3250 -1.6870 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7162 1.1941 -1.6077 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0798 0.0348 -0.7751 C 0 0 1 0 0 0 0 0 0 0 0 0 4.5269 -0.2834 -0.6624 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8462 -1.4358 -1.6289 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4628 0.8258 -1.0283 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6900 -0.8074 0.7232 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2862 -0.8140 1.3672 C 0 0 2 0 0 0 0 0 0 0 0 0 2.7638 -2.1619 1.4610 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7651 -2.6286 0.8965 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4393 -3.1026 2.2856 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5639 0.2301 0.6357 C 0 0 2 0 0 0 0 0 0 0 0 0 2.9946 1.5620 1.2152 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6262 -0.1756 1.4992 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0249 -0.1202 0.0537 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0882 1.9522 0.9704 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6328 1.7447 2.1167 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.9719 3.0448 0.8806 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.3208 -4.2065 1.3665 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2052 -2.8352 2.5960 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1617 -2.9706 -1.3555 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8152 -2.3388 -1.3152 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4565 -3.9252 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8569 -0.7002 1.9910 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9185 -1.3302 0.0675 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9074 0.0495 1.1881 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9099 1.2349 -0.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8705 0.0267 -1.7040 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7088 2.0718 -2.1386 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9560 3.0064 -0.8572 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0090 2.4224 -1.8295 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7563 1.0941 -2.6881 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2100 -1.6001 -0.8545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5283 -0.7711 -2.3692 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1262 -1.0377 -1.8556 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6848 1.3029 1.0560 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7970 -1.6177 1.1268 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5673 -0.6547 2.3961 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8628 -0.6431 2.4995 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1934 0.9762 2.3604 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8931 -0.8562 0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7860 2.8579 0.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8337 3.2976 -0.3535 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5567 2.6050 1.2436 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0515 2.3854 -2.0585 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8252 0.7256 -2.5451 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0561 0.9549 -2.6627 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2229 2.1436 -1.3830 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5532 -0.8597 -1.1701 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1740 -1.3449 -2.4858 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7181 -2.4192 -1.0888 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9069 -1.4040 -1.9460 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4223 0.3845 -1.4339 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7819 1.4673 -0.1970 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0572 1.4139 -1.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9902 -1.9019 0.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4988 -0.4378 2.4163 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9023 -3.8575 2.7376 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4918 1.6182 2.2256 H 0 0 0 0 0 0 0 0 0 0 0 0 4.0677 1.4908 1.4694 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8424 2.4236 0.5829 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5108 -0.5628 1.3056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9939 -0.6263 -0.9603 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9329 3.8003 1.5594 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 2 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 1 0 10 11 1 6 10 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 1 16 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 21 24 1 0 24 25 1 0 25 26 1 0 26 27 2 0 26 28 1 0 25 29 1 0 29 30 1 1 24 31 1 0 12 32 1 0 7 33 1 1 33 34 2 0 33 35 1 0 32 4 1 0 32 7 1 0 16 10 1 0 29 20 1 0 29 15 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 3 40 1 0 4 41 1 1 5 42 1 0 5 43 1 0 6 44 1 0 6 45 1 0 8 46 1 0 8 47 1 0 9 48 1 0 9 49 1 0 11 50 1 0 11 51 1 0 11 52 1 0 12 53 1 1 13 54 1 0 13 55 1 0 14 56 1 0 14 57 1 0 15 58 1 6 17 59 1 0 17 60 1 0 17 61 1 0 18 62 1 0 18 63 1 0 19 64 1 0 19 65 1 0 20 66 1 6 22 67 1 0 22 68 1 0 22 69 1 0 23 70 1 0 23 71 1 0 23 72 1 0 24 73 1 6 25 74 1 1 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 31 79 1 0 32 80 1 6 35 81 1 0 M END

Standard InCHIKey	WLCHQSHZHFLMJH-VILVJDKQSA-N
Standard InCHI	InChI=1S/C30H46O5/c1-16(2)17-10-13-30(25(34)35)15-14-27(5)18(21(17)30)8-9-20-28(27,6)12-11-19-26(3,4)23(31)22(24(32)33)29(19,20)7/h17-23,31H,1,8-15H2,2-7H3,(H,32,33)(H,34,35)/t17-,18+,19-,20-,21+,22+,23-,27+,28+,29-,30-/m0/s1
SMILES	C=C(C)[C@@H]1CC[C@@]2(CC[C@]3(C)[C@H](CC[C@H]4[C@@]3(C)CC[C@H]3C(C)(C)[C@H]([C@H](C(=O)O)[C@]43C)O)[C@@H]12)C(=O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	486.33	Volume:	520.695 ? Van der Waals volume.
Dense:	0.934	LogP:	3.409 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.844 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.159 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	3.0	Rigid Bonds:	27.0
TPSA:	94.83 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.425	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.978	Fsp³:	0.867
MCE-18:	108.571 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.747	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.005 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.331	Promiscuous compounds:	0.122

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.416	MDCK Permeability:	-5.029
Pgp-inhibitor:	0.0	Pgp-substrate:	0.005
PAMPA:	0.996 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.04	30% Bioavailability (F30%):	0.047
50% Bioavailability (F50%):	0.726

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.216	MRP1:	0.998
Plasma Protein Binding (PPB):	95.117%	Volume Distribution (VD):	-0.411
Fu:	5.731% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.009
BSEP inhibitor:	0.061

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.375	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.096
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.004
HLM stability:	0.0 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

1.6

Half-life (T1/2):

1.476

ADMET: Toxicity

hERG Blockers:	0.022	hERG Blockers (10um):	0.016
Human Hepatotoxicity (H-HT):	0.651	Drug-induced Liver Injury (DILI):	0.801
AMES Toxicity:	0.177	Rat Oral Acute Toxicity:	0.234
Maximum Recommended Daily Dose:	0.196	Skin Sensitization:	0.975
Carcinogencity:	0.773	Eye Corrosion:	0.204
Eye Irritation:	0.844	Respiratory Toxicity:	0.871
Drug-induced Neurotoxicity:	0.01	Ototoxicity:	0.614
Hematotoxicity:	0.579	Drug-induced Nephrotoxicity:	0.903
Genotoxicity:	0.713	RPMI-8226 Immunitoxicity:	0.013
A549 Cytotoxicity:	0.006	Hek293 Cytotoxicity:	0.021
BCF:	0.453 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.396 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.956 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.278 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32998	zizyphus cambodiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18842418]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22989532]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27617953]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	Roots	n.a.	n.a.	PMID[28257196]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4792	Ziziphus mauritiana	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5986	Ziziphus jujuba	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]

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	Organism Name	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	5
Activity	8
Survival	2

Activity Type	# Activity
Individual protein	1
Cell line	8
Others	5
Non-molecular	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1896	Individual protein	Zinc finger protein GLI1	Homo sapiens	IC50	>	200000.0	nM	PMID[18842418]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT461	Cell line	PANC-1	Homo sapiens	IC50	=	195000.0	nM	PMID[18842418]
NPT90	Cell line	DU-145	Homo sapiens	IC50	>	200000.0	nM	PMID[18842418]
NPT80	Cell line	Raji	Homo sapiens	Activity	=	60.0	%	PMID[19481937]
NPT80	Cell line	Raji	Homo sapiens	Activity	>	80.0	%	PMID[19481937]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	IC50	>	10000.0	nM	PMID[27617953]
NPT2	Others	Unspecified	n.a.	Activity	=	8.5	%	PMID[19481937]
NPT2	Others	Unspecified	n.a.	Activity	=	35.7	%	PMID[19481937]
NPT2	Others	Unspecified	n.a.	Activity	=	72.1	%	PMID[19481937]
NPT2	Others	Unspecified	n.a.	Activity	=	100.0	%	PMID[19481937]
NPT2	Others	Unspecified	n.a.	IC50	=	400.0	molar ratio	PMID[19481937]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT377	Cell line	OVCAR-3	Homo sapiens	Survival	=	68.0	%	PMID[9834149]
NPT165	Cell line	HeLa	Homo sapiens	Survival	=	65.0	%	PMID[9834149]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

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 toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC211162 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	23951
0.1-0.2	23184
0.2-0.3	2386
0.3-0.4	239
0.4-0.5	48
0.5-0.6	31
0.6-0.7	12
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC183374
0.8448	Intermediate Similarity	NPC195395
0.6667	Remote Similarity	NPC264317
0.6667	Remote Similarity	NPC294438
0.6667	Remote Similarity	NPC80590
0.6562	Remote Similarity	NPC24772
0.6562	Remote Similarity	NPC488506
0.6562	Remote Similarity	NPC220498
0.6308	Remote Similarity	NPC488164
0.6308	Remote Similarity	NPC264005
0.6176	Remote Similarity	NPC486704
0.6061	Remote Similarity	NPC213832
0.6032	Remote Similarity	NPC68828
0.6	Remote Similarity	NPC119743
0.597	Remote Similarity	NPC201655
0.5882	Remote Similarity	NPC16377
0.5821	Remote Similarity	NPC291373
0.5797	Remote Similarity	NPC475061
0.5781	Remote Similarity	NPC246445
0.5758	Remote Similarity	NPC192744
0.5652	Remote Similarity	NPC2783
0.5652	Remote Similarity	NPC151191
0.5571	Remote Similarity	NPC488213
0.5507	Remote Similarity	NPC271974
0.5507	Remote Similarity	NPC277399
0.5507	Remote Similarity	NPC247312
0.5493	Remote Similarity	NPC488165
0.5429	Remote Similarity	NPC4309
0.5375	Remote Similarity	NPC486706
0.5375	Remote Similarity	NPC486705
0.5352	Remote Similarity	NPC474719
0.5352	Remote Similarity	NPC269360
0.5352	Remote Similarity	NPC601275
0.5316	Remote Similarity	NPC486709
0.5309	Remote Similarity	NPC486708
0.5278	Remote Similarity	NPC160506
0.5205	Remote Similarity	NPC478841
0.5205	Remote Similarity	NPC488166
0.5205	Remote Similarity	NPC169933
0.5205	Remote Similarity	NPC601176
0.5181	Remote Similarity	NPC290349
0.5122	Remote Similarity	NPC486699
0.5116	Remote Similarity	NPC97475
0.5116	Remote Similarity	NPC486696
0.5068	Remote Similarity	NPC611139

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC211162 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6000
0.1-0.2	3080
0.2-0.3	67
0.3-0.4	0
0.4-0.5	1
0.5-0.6	1
0.6-0.7	1
0.7-0.8	0
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
0.6667	Remote Similarity	NPD7520	Phase 1
0.5278	Remote Similarity	NPD8035	Phase 2

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by 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