NPASS Compound

Natural Product: NPC231712

Natural Product ID	NPC231712
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Isohopeaphenol A
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL510147
PubChem CID	11967401
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0003405] 2-arylbenzofuran flavonoids

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 110121 0 0 0 0 0 0 0 0999 V2000 0.1593 1.0427 -3.3598 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0335 0.8013 -4.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2051 0.3968 -5.1918 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2871 0.2380 -4.3578 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1151 0.4913 -3.0152 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9094 0.8921 -2.4941 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7417 1.1819 -1.0335 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0014 1.6061 -0.4376 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9804 1.0232 0.3322 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0106 1.7672 0.8159 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0936 3.1285 0.5311 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1408 3.7392 -0.2363 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1107 2.9807 -0.7102 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1215 3.6144 -1.5054 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1605 3.8687 1.0362 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1599 -0.4176 0.7156 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.2792 -1.2747 -0.1467 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0043 -1.1082 -0.6320 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5060 -2.0569 -1.4918 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2495 -3.1551 -1.8645 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5143 -3.3194 -1.3778 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0492 -2.3724 -0.5054 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2718 -2.2958 0.1199 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.5255 -0.8716 0.2583 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6301 -0.7427 1.2265 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4883 -1.2012 2.5105 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.5731 -1.1271 3.3870 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7692 -0.5962 2.9544 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.9034 -0.1364 1.6595 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.8364 -0.2088 0.7953 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.8351 -0.5308 3.8385 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7531 -4.1211 -2.7334 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0495 -0.0251 -0.3922 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3940 0.2223 1.0200 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1596 1.5544 0.9136 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3921 2.6052 1.3446 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8252 3.9044 1.2737 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0721 4.1469 0.7506 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8911 3.1025 0.3007 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4074 1.8084 0.4001 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5483 0.9270 0.0017 C 0 0 1 0 0 0 0 0 0 0 0 0 3.1844 -0.4287 -0.2538 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8583 -1.0946 -1.2523 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6925 -2.4450 -1.5236 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8170 -3.1627 -0.7686 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1214 -2.5348 0.2356 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2817 -1.2036 0.5036 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4160 -0.6878 1.5977 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0300 -1.6649 2.5934 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0909 -2.2005 3.3444 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9200 -3.1222 4.3476 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6557 -3.5371 4.6275 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4014 -3.0420 3.9223 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2132 -2.1161 2.9169 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4276 -4.4689 5.6338 O 0 0 0 0 0 0 0 0 0 0 0 0 1.2274 -3.2947 0.9948 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3889 -3.0955 -2.5412 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2857 1.7634 -0.9417 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7690 1.5544 -0.7946 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5996 1.2024 -1.8279 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9404 1.0547 -1.5846 C 0 0 0 0 0 0 0 0 0 0 0 0 8.5041 1.2446 -0.3354 C 0 0 0 0 0 0 0 0 0 0 0 0 7.6810 1.5998 0.7166 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3117 1.7503 0.4654 C 0 0 0 0 0 0 0 0 0 0 0 0 9.8670 1.0846 -0.1325 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1371 3.0653 -0.2560 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0682 4.9860 1.7033 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4176 0.1314 -6.5425 O 0 0 0 0 0 0 0 0 0 0 0 0 1.1216 1.3599 -2.9622 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8337 0.9057 -5.4084 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2458 -0.0771 -4.7499 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9955 0.3690 -2.3521 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0084 2.0436 -0.9871 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7802 1.3643 1.4785 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2024 4.8182 -0.4672 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4362 4.0252 -2.3645 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9378 4.7468 1.4960 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9960 -0.5947 1.7668 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4835 -1.9920 -1.9507 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1366 -4.1722 -1.6433 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7515 -0.4968 -0.7488 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5733 -1.6141 2.8618 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4329 -1.4931 4.3834 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.8642 0.2699 1.3755 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9829 0.1623 -0.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.5913 0.1305 3.6942 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3736 -4.7324 -3.2402 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8571 -0.1758 -1.0515 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4642 0.4298 1.6500 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6017 2.4594 1.7934 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4706 5.1584 0.6661 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2103 0.8363 0.9875 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5355 -0.5781 -1.8739 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6445 -4.2292 -0.9315 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1461 0.0055 2.1761 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1235 -1.8981 3.1566 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7717 -3.5177 4.9121 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4408 -3.3523 4.1178 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0415 -1.7202 2.3596 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8305 -5.3857 5.5913 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8091 -4.1227 0.6105 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3916 -2.9814 -2.6618 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9476 1.8245 -1.9642 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1546 1.0526 -2.8131 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5790 0.7742 -2.4237 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0829 1.7586 1.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7373 2.0371 1.3333 H 0 0 0 0 0 0 0 0 0 0 0 0 10.5301 1.0583 -0.8941 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4657 5.4738 1.0135 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7884 -0.7507 -6.8680 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 2 0 12 13 1 0 13 14 1 0 11 15 1 0 9 16 1 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 2 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 26 27 1 0 27 28 2 0 28 29 1 0 29 30 2 0 28 31 1 0 20 32 1 0 18 33 1 0 33 34 1 0 34 35 1 0 35 36 2 0 36 37 1 0 37 38 2 0 38 39 1 0 39 40 2 0 40 41 1 0 41 42 1 0 42 43 2 0 43 44 1 0 44 45 2 0 45 46 1 0 46 47 2 0 47 48 1 0 48 49 1 0 49 50 2 0 50 51 1 0 51 52 2 0 52 53 1 0 53 54 2 0 52 55 1 0 46 56 1 0 44 57 1 0 41 58 1 0 58 59 1 0 59 60 2 0 60 61 1 0 61 62 2 0 62 63 1 0 63 64 2 0 62 65 1 0 58 66 1 0 37 67 1 0 3 68 1 0 6 1 1 0 33 7 1 0 48 34 1 0 54 49 1 0 64 59 1 0 13 8 2 0 24 16 1 0 30 25 1 0 40 35 1 0 47 42 1 0 22 17 1 0 66 39 1 0 1 69 1 0 2 70 1 0 4 71 1 0 5 72 1 0 7 73 1 6 10 74 1 0 12 75 1 0 14 76 1 0 15 77 1 0 16 78 1 1 19 79 1 0 21 80 1 0 24 81 1 6 26 82 1 0 27 83 1 0 29 84 1 0 30 85 1 0 31 86 1 0 32 87 1 0 33 88 1 6 34 89 1 1 36 90 1 0 38 91 1 0 41 92 1 1 43 93 1 0 45 94 1 0 48 95 1 1 50 96 1 0 51 97 1 0 53 98 1 0 54 99 1 0 55100 1 0 56101 1 0 57102 1 0 58103 1 6 60104 1 0 61105 1 0 63106 1 0 64107 1 0 65108 1 0 67109 1 0 68110 1 0 M END

Standard InCHIKey	YQQUILZPDYJDQJ-CMUHVXPYSA-N
Standard InCHI	InChI=1S/C56H42O12/c57-29-9-1-25(2-10-29)45-47-37(17-33(61)21-41(47)65)53-49-39(19-35(63)23-43(49)67-55(53)27-5-13-31(59)14-6-27)51(45)52-40-20-36(64)24-44-50(40)54(56(68-44)28-7-15-32(60)16-8-28)38-18-34(62)22-42(66)48(38)46(52)26-3-11-30(58)12-4-26/h1-24,45-46,51-66H/t45-,46-,51-,52+,53+,54+,55-,56-/m0/s1
SMILES	c1cc(ccc1[C@H]1c2c(cc(cc2O)O)[C@@H]2c3c(cc(cc3O[C@H]2c2ccc(cc2)O)O)[C@@H]1[C@@H]1c2cc(cc3c2[C@@H](c2cc(cc(c2[C@@H]1c1ccc(cc1)O)O)O)[C@H](c1ccc(cc1)O)O3)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	906.27	Volume:	916.662 ? Van der Waals volume.
Dense:	0.989	LogP:	5.255 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.048 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-6.624 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	64.0
TPSA:	220.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	12.0
H-Bond Donor:	10.0	Rings:	12.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.078	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.117	Fsp³:	0.143
MCE-18:	221.0 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	1.0	Fluc inhibitor:	0.848 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.096 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.33 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.67	Promiscuous compounds:	0.232

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.551	MDCK Permeability:	-4.791
Pgp-inhibitor:	0.0	Pgp-substrate:	0.976
PAMPA:	0.003 ? 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%):	0.985	30% Bioavailability (F30%):	1.0
50% Bioavailability (F50%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.998
Plasma Protein Binding (PPB):	90.298%	Volume Distribution (VD):	-0.105
Fu:	13.816% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.301
BSEP inhibitor:	0.986

ADMET: Metabolism

CYP1A2-inhibitor:	0.973	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.965	CYP2C19-substrate:	0.646
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.004
CYP2D6-inhibitor:	0.989	CYP2D6-substrate:	0.997
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.79
HLM stability:	0.995 ? 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):

2.207

Half-life (T1/2):

5.189

ADMET: Toxicity

hERG Blockers:	0.635	hERG Blockers (10um):	0.914
Human Hepatotoxicity (H-HT):	0.998	Drug-induced Liver Injury (DILI):	0.079
AMES Toxicity:	0.822	Rat Oral Acute Toxicity:	0.384
Maximum Recommended Daily Dose:	1.0	Skin Sensitization:	0.996
Carcinogencity:	0.015	Eye Corrosion:	0.0
Eye Irritation:	0.776	Respiratory Toxicity:	0.632
Drug-induced Neurotoxicity:	0.627	Ototoxicity:	0.967
Hematotoxicity:	0.002	Drug-induced Nephrotoxicity:	0.396
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.022
A549 Cytotoxicity:	0.994	Hek293 Cytotoxicity:	1.0
BCF:	1.162 ? 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:	5.904 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.903 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	6.012 ? 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
NPO32506	Vatica oblongifolia	Species	Dipterocarpaceae	Eukaryota	stem bark	n.a.	n.a.	PMID[12444676]

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
MIC	2

Activity Type	# Activity
Organism	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT602	Organism	Mycobacterium smegmatis	Mycobacterium smegmatis	MIC	>	100.0	ug.mL-1	PMID[25734623]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100.0	ug.mL-1	PMID[25734623]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

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 NPC231712 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	31255
0.1-0.2	16729
0.2-0.3	1705
0.3-0.4	114
0.4-0.5	21
0.5-0.6	9
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	3

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC242774
1.0	High Similarity	NPC224921
1.0	High Similarity	NPC237546
0.8333	Intermediate Similarity	NPC233886
0.7164	Intermediate Similarity	NPC180605
0.7059	Intermediate Similarity	NPC122980
0.7059	Intermediate Similarity	NPC148516
0.7059	Intermediate Similarity	NPC107862
0.7059	Intermediate Similarity	NPC177172
0.6944	Remote Similarity	NPC105073
0.6944	Remote Similarity	NPC224528
0.6818	Remote Similarity	NPC488747
0.6707	Remote Similarity	NPC48880
0.6567	Remote Similarity	NPC174787
0.6567	Remote Similarity	NPC213607
0.6324	Remote Similarity	NPC120633
0.625	Remote Similarity	NPC176804
0.625	Remote Similarity	NPC71686
0.6232	Remote Similarity	NPC473018
0.6212	Remote Similarity	NPC157081
0.6027	Remote Similarity	NPC261896
0.5467	Remote Similarity	NPC218801
0.5366	Remote Similarity	NPC111134
0.5352	Remote Similarity	NPC149633
0.5263	Remote Similarity	NPC97578
0.5238	Remote Similarity	NPC9292
0.5238	Remote Similarity	NPC145659
0.5211	Remote Similarity	NPC478982
0.5205	Remote Similarity	NPC182509
0.5205	Remote Similarity	NPC329836

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC231712 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6621
0.1-0.2	2487
0.2-0.3	36
0.3-0.4	6
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
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
		NPD

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